Careers and the Business of Law

In this episode, we sit down with Nathan Walter, CEO and co-founder of BriefPoint, live TLTF. Nathan's unique story combines the passion of a founder, the skills of a technologist, and the determination to solve one of litigation's most pressing challenges: the inefficiency and cost of document preparation. Whether you're a legal professional or an aspiring entrepreneur, this conversation is packed with insights and inspiration.

What You'll Hear in This Episode:

• The Origin of BriefPoint: Learn how Nathan's frustration as a litigator led to creating a tool that automates discovery responses and requests, saving attorneys countless hours and leveling the playing field in litigation.
• Legal Aid Impact: Hear how organizations like the Legal Aid Foundation of Los Angeles are using BriefPoint to enhance efficiency and focus on impactful legal work.
• Founders' Journey: Nathan shares how he met his co-founder, Chris Maffin, while playing online video games and how they've built a nimble, high-performing team of four that's solving real-world problems.
• Inspiration and Resources: Nathan's top book recommendations for founders include:
  • High Output Management by Andrew Grove
  • Crossing the Chasm by Geoffrey Moore
  • Comedy Writing Secrets by Mark Shatz

Why Listen?

Nathan's passion for innovation and his unique perspective as both a litigator and tech entrepreneur make this episode a must-listen for anyone interested in legal technology, entrepreneurship, or the intersection of tech and law.

Connect with Nathan:

• Website: BriefPoint
• LinkedIn: Nathan Walter

If you enjoyed this episode, don't forget to like, share, and subscribe. Let's take your career from now to next.

Never eat alone.

In this episode, we're joined by Carla Swansburg, CEO of ClearyX, live from TLTF. Carla's incredible journey spans 20+ years in law firms, corporate leadership, and operations innovation at Epic, culminating in her role as CEO of ClearyX—a bold initiative to reimagine how law firms innovate and serve clients.

What You'll Hear in This Episode:

• ClearyX's Mission: Learn how ClearyX is leveraging its independence from Cleary Gottlieb to disrupt traditional law firm models, building bespoke solutions that put client needs first.
• Disrupting from Within: Inspired by Clayton Christensen's Innovator's Dilemma, Carla explains how ClearyX is addressing inefficiencies, embracing technology, and challenging the status quo in the legal industry.
• The Talent Advantage: Why a fresh, modern approach to work—fully remote teams, geographical freedom, and flexible roles—is key to attracting top talent in a competitive market.
• Building Better Solutions: Carla's vision for combining technology, consulting, and operational services into tailored solutions that serve clients more effectively than ever.

Why Listen? Carla's candid insights will resonate with legal professionals, innovators, and anyone interested in how traditional industries are adapting to 21st-century challenges. Her approach to leadership, talent, and innovation offers actionable inspiration for rethinking the business of law.

Enjoyed this episode? Share it, subscribe, and leave us a review! Join the conversation as we explore what's next for legal tech and innovation.

Never eat alone. Let's take this journey from now to next!

In this episode, we're joined by Casey Tierney, investor and leader at TLTF, live from Key Biscayne, Florida. Casey is the driving force behind TLTF's startup and scale showcases, helping connect funders and founders to accelerate legal tech innovation. From her start as a bank teller in South Carolina to evaluating groundbreaking startups, Casey's journey is a testament to grit, curiosity, and vision.

What You'll Hear in This Episode:

• Valuing Innovation: Casey shares how her early career in valuation shaped her perspective on the art and science of assessing companies—and how that translates to today's legal tech startups.
• Behind the Startup Showcase: Hundreds of applications, 22 startups selected—Casey breaks down how TLTF curates its startup and scale stages to highlight the best of the best.
• What Investors Look For: Passion, grit, and product-market fit. Learn what Casey and her team prioritize when evaluating early-stage companies in the legal tech ecosystem.
• The Role of Generative AI: How platforms like ChatGPT and Gemini are reshaping the way investors and startups operate—and why adoption, not just technology, will define the future of legal innovation.
• A Career in Investing: Casey gives a behind-the-scenes look at her day-to-day, from back-to-back founder meetings to leveraging AI for smarter, faster decision-making.
• Book Talk: Casey's resolution to read only books older than 50 years has led her to rediscover classics like 1984 and Gone with the Wind—and it might just inspire your next reading list.

Why Listen? This episode is packed with insights for anyone interested in legal tech, startup ecosystems, or breaking into a career in venture investing. Casey's practical advice and big-picture vision make this a must-listen for innovators and dreamers alike.

Enjoyed this conversation? Share it, subscribe, and leave us a review! Let's connect the dots from now to next.

Never eat alone. Let's build the future of legal tech together.

In this episode, we sit down with Roxanne Petraeus, CEO and co-founder of Ethena, live from TLTF. With a background spanning the U.S. Army, Harvard, and McKinsey, Roxanne brings a unique perspective to reimagining compliance as more than just a checkbox—she's building a culture-driven revolution.

What You'll Hear in This Episode:

• From Army to Ethena: How Roxanne's military experience shaped her understanding of leadership, culture, and ethics—and how that translates into compliance done right.
• Reinventing Compliance: Why traditional compliance training doesn't work and how Ethena is transforming it into a culture-building tool that drives real behavior change.
• Innovation in Action: Roxanne shares how Ethena works with companies like Figma, Notion, and Pinterest, while also scaling solutions for massive banks and telecoms.
• Lessons for Founders: From raising $50M in funding to navigating the emotional rollercoaster of startup life, Roxanne offers insights for entrepreneurs on building and scaling a business.
• What's Next for Compliance: AI ethics, whistleblower hotlines, and a proactive approach to the ever-evolving regulatory landscape.

Why Listen? Roxanne's grit and clarity will inspire you to think differently about compliance, leadership, and what it takes to build something transformative in a legacy industry. Plus, check out Grit by Angela Duckworth for more on the power of perseverance and passion.

Love this episode? Share it, subscribe, and leave us a review! Find out how to connect with Roxanne on LinkedIn and learn more about Ethena's mission to reshape compliance for the modern age.

Listen now! Never eat alone. Let's take this journey from now to next.

Join us live from TLTF, as we sit down with Catherine Kemnitz, Chief Strategy and Development Officer at Axiom, for a no-holds-barred discussion on the future of legal tech, talent, and innovation.

What You'll Hear in This Episode:

• Gen AI's Impact: Catherine unpacks why generative AI is the "wrecking ball" disrupting legal tech—and why there's no turning back.
• Evolving Talent Expectations: Discover why the next generation of lawyers demand innovation and why firms stuck in the past risk irrelevance.
• Lessons in Change: Catherine shares wisdom from decades at the forefront of legal tech and explains how embracing risk (and letting go of fear) is the key to thriving in this new era.

Why Listen? This episode will leave you rethinking the legal industry's future and your role in shaping it. Catherine's insights are sharp, inspiring, and packed with practical takeaways for funders, founders, and future-focused professionals.

Love what you heard? Subscribe, share, and leave us a review! Let's push the boundaries of what's possible—together.

Listen now!

🔗 Episode Highlights: In this episode, David Cowen sits down with Jon Bartman, Co-Founder of The Law Tech Consultancy. Jon shares his journey as a global connector for legal tech innovators, offering sharp insights into the latest industry trends ahead of the TLTF Summit (Dec. 4-6 in Miami). 💡 What You'll Learn:

• "Turning Acorns into Unicorns": How Jon helps legal tech startups refine strategies, connect with buyers, and scale globally.
• The Pace of Legal Innovation: Why the last 24 months have been transformative for legal tech, and how startups are outpacing adoption rates in law firms.
• TLTF Startup Showcase: Behind the scenes with Jon as a judge, evaluating innovative, market-ready legal tech solutions.
• Leadership and Vision: How talent shifts and strategic investments signal the rise of new contenders like Kirkland & Ellis in the innovation landscape.

🎶 Closing Vibe: As a lifelong music enthusiast, Jon dives into his love for Steely Dan, R&B, and Tyler, the Creator. He reflects on how pushing boundaries in music parallels innovation in legal tech. Special Mentions:

• Jon Bartman
• Zach Posner
• Rebecca Engel
• TLTF Summit
• Esther Bowers
• Kirkland & Ellis

🚀 Don't Miss Out: Subscribe to Careers in the Business of Law for exclusive insights from legal innovators like Jon Bartman. Catch Jon and David at the TLTF Summit in Miami, Dec. 4-6. Available now on Apple Podcasts, Spotify, or your favorite platform!

🔗 Episode Highlights:

In this episode, David Cowen sits down with Wendy Chow, General Counsel at Cityblock Health, who shares her journey from the Visiting Nurse Service of New York to leading legal strategy at a fast-growing, mission-driven startup. As a TLTF Advisory Board member, Wendy offers a fresh perspective on legal operations, innovation, and leadership ahead of the upcoming TLTF Summit (Dec. 4-6 in Miami). 💡 What You'll Learn:

• Generative AI in Legal: How Wendy leverages Gen AI to boost efficiency, team engagement, and operational outcomes.
• TLTF Experience: Wendy's path from first-time attendee to advocate, championing more in-house counsel at this "curated, engaging, and fun" conference.
• Leadership Lessons: Why hiring a LegalOps expert first transformed her approach to building efficient, business-oriented legal teams.
• Cityblock's Mission: How the company innovates healthcare for Medicaid and dual-eligible populations through a unique venture-backed model.

🎶 Closing Vibe: With Fleetwood Mac's timeless tunes in the background, Wendy shares her love for thoughtful legal tech solutions and gives a special shout-out to Kathy of Streamline AI for her game-changing product design. Special Mentions:

• Wendy Chow - Cityblock Health
• Zach Posner
• Rebecca Engel
• Kathy M. Zhu
• TLTF Summit

🚀 Don't Miss Out: Subscribe to Careers in the Business of Law for exclusive insights into the future of legal innovation. Catch Wendy and David at the TLTF Summit in Miami, Dec. 4-6. Available now on Apple Podcasts, Spotify, or your favorite platform!

🔗 Episode Highlights: In this episode, David Cowen chats with Dr. Hemma Lomax, a compliance trailblazer whose journey spans the US SEC, Disney, Snap, Zendesk, and now COMPAAS 360. As an advisor for the upcoming TLTF Summit (Dec. 4-6 in Miami), Dr. Lomax shares her bold vision for transforming compliance and legal tech.💡

What You'll Learn:

1. Innovation in Compliance: Why Dr. Lomax believes compliance should feel like Waze—guiding employees and customers with ease, not friction.
2. Inside TLTF: The "casino of innovation" connecting funders, founders, and customers to co-create groundbreaking legal tech solutions.
3. Personal Mission: How a Ph.D. in human rights law inspired her to operationalize integrity in corporate governance.

🎶 Closing Vibe: With Otis Redding's "Mr. Pitiful" playing us out, Dr. Lomax reminds us that embracing criticism and unmet needs fuels entrepreneurial breakthroughs.

🚀 Don't Miss Out: Subscribe to Careers in the Business of Law for exclusive insights into the future of law and join the conversation at the TLTF Summit. Available now on Apple Podcasts, Spotify, or your favorite platform!

🔥 Episode Highlights: In this inspiring and deeply insightful episode, David Cowen sits down with Kelly Friedman—Chief Legal Data Intelligence Officer and Senior Counsel at Heuristica Discovery Counsel LLP and a pioneer in the legal tech space. Kelly is breaking new ground, leading the charge in Legal Data Intelligence (LDI) and making waves across the industry. With her passion for music, an impressive playlist of 2,500 songs, and her dedication to changing how we think about data in law, she's a trailblazer you won't want to miss. Key Moments:

• [0:34] Meet Kelly, a founding member of Legal Data Intelligence (LDI) and a big believer in the future of legal tech.
• [1:10] Kelly's journey from commercial litigator to e-discovery business leader and now Chief LDI Officer.
• [3:10] The rise of the "Legal Data Intelligence Officer" title and how it's reshaping the industry.
• [6:00] Why legal decisions today demand more than just a "left-to-right" approach – understanding data in 3D.
• [19:46] LDI's Architects Program—connecting LDI experts and innovators to collaborate on evolving models.

🎶 Music Meets Law Kelly's theme song, "I Can Do It with a Broken Heart" by Taylor Swift, fuels her drive. As she says, this song embodies resilience—a value she brings to every challenge in her career. 🌍 Why Listen? If you're looking to stay on the cutting edge of legal tech or want to know what it's like to lead in the high-stakes world of data intelligence, this episode is a must-hear! Kelly's journey and her perspective on data-driven decision-making offer invaluable insights, especially if you're a litigator, in-house counsel, or legal tech enthusiast. 💬 Be Part of the Conversation: Connect with like-minded professionals, explore career advancement tips, and hear from those leading the future of law. Don't miss out—subscribe and never miss an episode of Careers in the Business of Law! 🎙 Subscribe on Apple Podcasts, Spotify, or your favorite platform to stay tuned for more career-transforming conversations!

🎙️ Discover New Horizons in Legal Data Intelligence! Join David Cowen as he speaks with Brad Kolacinski from Control Risks in this enlightening episode. Brad shares how his expertise in e-discovery has expanded into broader legal, compliance, and even crisis management roles, leveraging data intelligence to solve new and complex challenges in today's business environment. 🔥 Episode Highlights:

• LDI Beyond E-discovery: Brad explains how Legal Data Intelligence is "so much more than e-discovery," applying its tools and processes to areas like cyber, compliance, and threat intelligence monitoring.
• Proactive Compliance & Threat Monitoring: Learn about Control Risks' proactive approach to threat monitoring, using AI, social media scraping, and data analytics to identify risks and prevent workplace violence.
• Creative Solutions for Global Challenges: Brad shares examples of how LDI is used creatively in real-world cases, from compliance monitoring to environmental litigation, using both traditional and external data sources.

🚀 Special Mentions:

• Brad Kolacinski - LinkedIn
• Relativity
• Ohana Fest

🎧 Tune in Now! This episode is packed with insights for anyone looking to expand their career in legal tech and data intelligence. Learn how Brad and his team are using innovative tools like AI and data analytics to provide proactive solutions for clients. Plus, discover Brad's passion for Pearl Jam as we close with his favorite band!