Explore every episode of the podcast Careers and the Business of Law

Will Seaton, Chief Customer Officer at DraftWise and former commercial lead at Palantir sits down with David Cowen to unpack what’s really changing at the intersection of AI, contracts, and legal careers. This conversation dives deep into the shift from prompt to context engineering, the rise of roles like forward deployed engineers, and why the future of legal work isn’t about replacing lawyers, it’s about scaling their judgment. If you're serious about where your team, talent, and tech are headed, this is the episode.

Key Topics Covered:

• What law firms and legal departments can learn from Palantir’s forward deployed model
• Why context, not prompts is the real power source behind GenAI in legal workflows
• The new business value of outside counsel: from selling information to selling judgment
• How tools like DraftWise unlock contract data and turn junior lawyers into high performers fast
• The evolution of roles in legal: from lawyers to context engineers, data strategists, and AI copilots
• Augmented intelligence > artificial intelligence: the case for keeping humans in the loop
• What legal AI tells us about the next wave in the demand and flow of talent

People & Ideas We Mentioned:

• Alex Karp, CEO of Palantir – the philosopher-CEO shaping how the world thinks about data and power
• Kyle Bahr from Cleary Gottlieb – sparking smart conversations on context engineering and where legal AI is headed
• Omar Haroun, founder of Eudia (formerly Text IQ) – pushing the boundaries on augmented intelligence in legal
• Song of the Day: “Celebrate” by Jordan Rakei – Will’s go-to morning track – Give it a listen

🎧 Subscribe on Apple Podcasts, Spotify, or wherever you listen. Share this episode and take your career from now to next!

💡To learn more about the future of legal innovation, visit https://cowengroup.com/

Never eat alone!

 

Bestselling author and “non-obvious” thinker Rohit Bhargava sits down with David Cowen for a high-energy, idea-packed conversation on creativity, persuasion, and building influence in unexpected ways. Drawing from his global bestseller and branding roots at Ogilvy and Leo Burnett, Rohit shares how to spot hidden patterns, spark change inside organizations, and bring others along the journey. If you’ve ever felt like the only one seeing around corners, this episode is for you.

Key Topics Covered:

• The 4 habits of non-obvious thinkers (and how to build them daily)
• Why ideas alone are worthless and what separates dreamers from doers
• The Einstein lesson: how to find (and be) your “Max Planck”
• Self-serving altruism: the underrated power move in building influence
• How to get others to join your vision without a “hard sell”
• The art of persuasive storytelling from someone trained at Ogilvy and Leo Burnett
• Why getting outside your echo chamber is the secret weapon for innovation

Speacial mention: Rohit’s latest bestseller, Non Obvious Thinking, is now available, don’t miss it. 

🎧 Subscribe on Apple Podcasts, Spotify, or wherever you listen. Share this episode and take your career from now to next!

💡To learn more about the future of legal innovation, visit https://cowengroup.com/

Never eat alone!

 

Frank Nuzzi, Senior IP Counsel at Siemens, joins David Cowen to unpack the mindset shift every legal professional needs right now. From sandboxing with Microsoft Copilot to pushing the boundaries of AI in legal workflows, this episode dives into how curiosity and experimentation, not perfection are shaping the next generation of legal work. If you're waiting for AI to be flawless before jumping in, you're already behind.

Key Topics Covered:

• Why “don’t be cheap on your career” might be the best AI advice you’ll hear
• The productivity edge: how Copilot saves time in Outlook and sharpens legal workflows
• Frank’s system for learning fast: white papers, eBooks, YouTube, and morning study
• How genAI accelerates legal research and boosts comprehension
• The reality of “time saved” in legal, quality over quantity
• Lessons from DHL’s legal playbooks and the power of asking “what if?”
• Why staying curious is the real ROI of AI tools

🎧 Subscribe on Apple Podcasts, Spotify, or wherever you listen. Share this episode and take your career from now to next!

💡To learn more about the future of legal innovation, visit https://cowengroup.com/

Never eat alone!

Catherine Jopling, General Counsel at MPW Industrial Services, doesn’t lead from behind a desk, she builds trust in the field, layer by layer. In this episode, she shares how she leads legal with empathy, curiosity, and proactive strategy in a decentralized, blue-collar business.

Instead of waiting for crises, Catherine gets ahead of them, visiting sites, meeting people where they are, and building systems that make legal a value driver, not a cost center. Whether she’s coding a risk registry in SharePoint or talking AI with her executive team, she proves that innovation doesn’t require big budgets, just resourcefulness and courage.

🎙 Highlights:

• Leading a lean team of 7 serving 4,000+ across North America
• Legal as a proactive partner, not a reactive fixer
• DIY tech: Building risk tools with ChatGPT + SharePoint
• Trust as the foundation, human connection > automation
• Leadership lessons from books, site visits, and Whitney Houston

💡 Takeaways:

• Build trust before it’s needed
• Innovate with what you have
• Legal can and should drive value
• AI is powerful, but relationships are everything

🎯 Try this:
Reconnect with someone in your org before you need to. And take one small step toward building something new, just like Catherine.

🎧 Subscribe on Apple Podcasts, Spotify, or wherever you listen. Share this episode and take your career from now to next!

💡To learn more about the future of legal innovation, visit https://cowengroup.com/

Never eat alone!

 

Live from the DHL Legal Innovation Summit, David Cowen sits down with Omar Haroun, co-founder of Eudia, to break down the shift from artificial intelligence to augmented intelligence. Together they unpack what’s actually happening in legal innovation: smarter workflows, real cost transformation, and human-machine collaboration at scale. This conversation goes deep from M&A disruption with DHL to the messy middle of change, to the opportunities ahead for those willing to live in the future. If you're trying to figure out how to adapt, evolve, and lead with AI at your side, start here.

What You’ll Learn:

• Why AI isn’t replacing lawyers but the ones who use it might
• The real reason behind layoffs (hint: it’s not just tech, it’s operational innovation)
• How DHL and Eudia are unbundling legal services and redefining M&A speed
• What it means to be a Pattern Breaker and why “messy middle” is where the magic happens

Don’t wait for the dust to settle.
If you're a seeker, striver, or top guard thinking out loud about AI, talent, and transformation, this one's for you.

🎧Subscribe. Share it with a co-conspirator. And if you're not living in the future yet… what's holding you back?

💡To learn more about the future of legal innovation, visit https://cowengroup.com/

Never eat alone!

 

What happens when you take legal operations, move it into finance, scale it globally, and build a team of 85 legal professionals inside a Fortune 500? You get Brian Edge’s world and it’s nothing short of groundbreaking.

Live from the DHL Legal Innovation Summit, David Cowen sits down with Brian, SVP of Legal Franchise & Integrity Shared Services at MasterCard, for a high-energy, human-centered conversation on the next evolution of legal ops. From creating capacity through shared services to layering AI on top of HI (human intelligence), this episode is about unlocking better work, better relationships, and better outcomes at scale.

What You’ll Learn:

• Why shared services might be the next big leap beyond traditional legal ops
• How MasterCard scaled legal support globally without outsourcing its soul
• The surprising power of empathy, data, and dashboards in shaping business outcomes
• How AI is enabling, not replacing human brilliance in legal service delivery

This is legal operations V.3, more collaborative, more strategic, more human.

🎧 Subscribe on Apple Podcasts, Spotify, or wherever you listen. Share this episode and take your career from now to next!

💡To learn more about the future of legal innovation, visit https://cowengroup.com/

Never eat alone!

 

 

In this raw and energizing conversation of Careers and The Business of Law from the DHL Legal Innovation Summit, David Cowen sits down with Matthew Smith, Executive Vice President of Business Developmentat Array, to talk about building trust, managing high-performing teams, making the leap into legal from healthcare, and navigating the “middle of the middle” of a career. From the fear of hearing no to the power of shutting up and listening, this is required listening for anyone climbing the jungle gym of leadership.

What You’ll Learn:

• How great leaders coach, not micromanage
• Why listening is the most powerful (and overlooked) sales move
• What it really means to lead in the “middle of the middle”
• How values, vision, and relationships shape the second half of a career

Like what you hear?
🎧 Subscribe. Share. Send to someone who needs a jolt of clarity. Because your career’s not a ladder, it’s a jungle gym. And the climb gets better when we do it together.

💡To learn more about the future of legal innovation, visit https://cowengroup.com/

Never eat alone!

 

Live from the DHL Legal Innovation Summit in Columbus, David Cowen sits down with Christina Wojcik, Head of Innovation & Partnerships at Pearson Ferdinand, for a high-energy conversation on the future of legal services. Christina breaks down what it means to build a truly tech-first law firm, no associates, no legacy systems, just streamlined, partner-led innovation. From back-office automation to smarter pricing models, this episode explores how law firms can operate leaner, move faster, and deliver more value in a rapidly evolving market.

Key Takeaways:

• Tech-first law firms are rethinking structure, no associates, just distributed, empowered partners
• Automating admin tasks frees up time, margin, and talent for high-value client work
• Clients want to partner on innovation, not just hear about it
• We’re in the messy middle of transformation, and the opportunity is wide open

🎧 Tune in, share with your team, and subscribe for more conversations that move legal from now to next.

Because careers aren’t ladders, they’re jungle gyms.

💡To learn more about the future of legal innovation, visit https://cowengroup.com/

Never eat alone!

 

 

In this episode of Careers and the Business of Law: The Legal Data Intelligence Series, David Cowen sits down with Richard Pachella, Strategic Alliance Advisor at Epiq, to unpack the seismic shifts happening across legal tech, operations, and talent.

If you're in eDiscovery, legal operations, or just trying to navigate your career in the age of AI, this episode is for you.

🔥 What you’ll hear:

• Why the smartest legal pros are leaning into AI now, not later
• How the lines between litigation support, M&A, regulatory, and compliance are blurring fast
• What today’s legal departments need: prompt engineers, strategic consultants, and legal technologists who think beyond the silo
• How LDI is transforming from a “think tank” to a “build tank”
• Practical ways to adopt GenAI tools in your day-to-day, starting today

📣 Plus: Rich drops a 60-second insider take on what Epiq is hiring for, and why diverse backgrounds are more valuable than ever.

🎧 If you’re serious about staying relevant, expanding your skills, and thinking out loud with the best in the business, press play!

💡To learn more about the future of legal innovation, visit https://cowengroup.com/

Never eat alone!

 

20 Years. 5 Pivots. 1 Big Bet on GenAI.

🎧 Featuring: Danny Thankachan | Head of Partnerships, CaseGuild

This isn’t your average industry chat. This is a high-voltage, real-talk conversation between two longtime insiders, David Cowen and Danny Thankachan on what really matters now in legal innovation, GenAI, and career growth.

📌 Highlights:

• The evolution of eDiscovery from 2004 to today
• Why Legal Data Intelligence (LDI) is more than a buzzword, it’s a framework for future-ready work
• Case Guild’s bold mission to reinvent internal investigations
• What career reinvention really looks like in the AI age
• And why your job might be disrupted but your career doesn’t have to be

🎧 Subscribe on Apple Podcasts, Spotify, or wherever you listen. Share this episode and take your career from now to next!

💡To learn more about the future of legal innovation, visit https://cowengroup.com/

Never eat alone!

 

Let’s get something straight: the job of General Counsel has left the building. Today’s GCs aren’t just legal advisors, they’re business architects, transformation leaders, and culture drivers. And if your legal team is still playing defense, you’re losing ground.

In this episode, Lisa Mather and Tim Fraser, two of the most forward-leaning legal execs in the game, pull back the curtain on how they’re redefining the GC role from the center of the business.

What you’ll walk away with:

• Why Legal Ops is outgrowing its old box and becoming strategic leadership.
• How the best GCs are operating at “120%” by speaking the language of margin, growth, and product.
• The mindset shift from “risk management” to “value creation” and what that means for your next hire.

🎯 Bonus:
Both Lisa and Tim will be live at the SOLID AI Agentic BootCamp at Microsoft this August and onstage at SOLID New York in September. Want to meet the First 50? Be there. Register here!

This isn’t incremental change. It’s an entirely new operating model.

Hit play. Share with your team. And start thinking out loud, together.

 

In this no-BS roundtable, David Cowen sits down with Kevin Cohn - Chief Customer Officer at Brightflag; Tyler Finn, Head of Community & Growth at SpotDraft; and Matthew Wheatley, VP, Client Strategy at Priori to unpack the real state of legal operations, talent, and transformation.

Forget the panel buzzwords. This episode pulls back the curtain on what’s actually happening inside high-performing legal teams. What’s inside:

• Legal ops has hit a plateau, but careers haven’t.
The smartest players are skipping the next rung and stepping into legal strategy, transformation, and C-suite alignment.

• There’s no ladder, just a jungle gym.
From executive assistants to legal COOs, this episode is a playbook for navigating ambiguity and turning it into an advantage.

• The real skill gap? It’s not tech. It’s knowing your value.
Are you a builder, a manager, or a creator? Know your lane, then double down.

This is the episode you forward to your team with one line:
“This is the conversation legal ops needs to hear right now.”                                                           

🎧 Subscribe on Apple Podcasts, Spotify, or wherever you listen. Share this episode and take your career from now to next!

💡To learn more about the future of legal innovation, visit https://cowengroup.com/

Never eat alone!

Headed to CLOC? So are E.J. Bastien and David Cowen and this episode is your field guide.

Before you start speed-walking the ARIA hallways and hunting for coffee and co-pilots, listen in. E.J. Bastien has spent two decades at Microsoft reimagining what in-house eDiscovery and litigation support can be. He’s leading teams, building AI agents, and solving tomorrow’s problems with tools that most legal teams haven’t even touched yet.

In this pre-CLOC masterclass, we dig into:

• How Microsoft is using GenAI to streamline review, code documents, and surface case-critical facts before a human ever sees them
• What it really means to build a bespoke agent trained on your legal team’s workflows not ChatGPT, but your playbook
• Why perfectionists are out, and “learn-it-alls” are in and how that mindset shift is the secret to surviving (and thriving) in 2025.

You’ll also hear what it takes to lead with confidence, experiment without fear, and stay grounded in the face of constant change.

It's Vegas. It's CLOC. It’s time to stop chasing answers and start trading playbooks.

🎧 Subscribe on Apple Podcasts, Spotify, or wherever you listen. Share this episode and take your career from now to next!

💡To learn more about the future of legal innovation, visit https://cowengroup.com/

Never eat alone!

Guest: Kevin Cohn, Chief Customer Officer, Brightflag
Host: David Cowen, President, The Cowen Group

🎙 This episode of Careers in the Business of Law (CBL) is a masterclass in motion.

Pre-live from the frontlines of CLOC, Kevin Cohn—Chief Customer Officer at Brightflag—joins David Cowen for a candid, strategic breakdown of how legal ops careers are being redefined in real time.

It’s not just theory. Kevin unpacks the real ROI of relationship-driven events, the anatomy of modern go-to-market strategy, and the emergence of legal ops as a strategic powerhouse inside the legal department.

🔑 Six Big Ideas from the Conversation

1. Community-first is the new go-to-market.
Bright Flag doesn’t lead with features—they lead with helping. Their playbook is about solving legal ops problems, not pitching products.

2. Events like CLOC drive Origination, Advancement, and Nurturing.
Think beyond booth traffic. Kevin outlines how events create momentum across the business development lifecycle—and why deep trust matters most.

3. Legal ops roles are moving up the strategy stack.
Titles like Chief Legal Data Officer and Legal Chief Strategy Officer mark a shift from execution to foresight. Legal ops is no longer the backstage crew—it’s co-authoring the future.

4. The champion persona is your north star.
Champions are the change agents inside legal departments. They may not control the budget, but they drive the decision.

5. First-time CLOC attendee? Come with a plan.
Ask questions. Introduce yourself. Set daily KPIs for connection. And before the rooftop parties blur your memory, write those names down.

6. Legal ops is leading the AI era.
While GCs are pulled into geopolitical and enterprise-wide risk, legal ops is best positioned to own digitization, AI integration, and operational change.

Viva Las Vegas. Let’s move from now to next.

What happens when a GC thinks like a CEO, rolls up his sleeves like a contractor, and leads like a startup founder? You get Mark Smolik, Chief Legal Officer of DHL Supply Chain, and a masterclass in legal leadership you can’t afford to miss.

This episode is a front-row seat to how Mark turned blue-collar grit, data discipline, and a sharp eye for ROI into a legal department that runs like a high-performance business unit. We unpack:

• His $37,000-a-claim insight that reshaped risk management.
• A bold AI deployment that eliminates human review in M&A due diligence.
• And the why behind DHL’s Legal Innovation Summit, June 3–4 in Columbus, where his full team will share the playbook.

If you’re wondering how to go from ideas to impact or how to just start, this is the episode. One of the best conversations we’ve had.

🎧 Subscribe on Apple Podcasts, Spotify, or wherever you listen. Share this episode and take your career from now to next!

💡To learn more about the future of legal innovation, visit https://cowengroup.com/

Never eat alone!

 

We’re not in Kansas anymore. We’re in the Jetsons Era.

Legal Data Intelligence isn’t just tech, it’s talent, timing, and the ability to see around corners.

In this episode, I sat down with Stacy Lettie, Chief of Staff to the General Counsel at Organon, and we went from Disney to data to dogs with AI collars. Yes, really.

We talked:

• Why the future of legal starts with foundations (Small World → Tron)
• What makes a great Chief of Staff
• When imposter syndrome disappears (spoiler: when you earn it)
• And the moment we decided—live, in-person—to build AI agents at Microsoft this July

🧠 Stacy brings the brains and heart. She’s a walking masterclass in Legal Ops > Strategy > LDI leadership.

Shoutout to the OGs of LDI—John Koss, Omar Haroun, Adam Rouse, Bobby Malhotra, Scott Milner, Farrah Pepper, Geoffrey Vance, and Julia Hasenzahl.

And to Jim Collins for the rocket fuel: If someone offers you a seat on a rocket ship, don’t ask which seat, just get on.

🎧 Subscribe on Apple Podcasts, Spotify, or wherever you listen. Share this episode and take your career from now to next!

💡To learn more about the future of legal innovation, visit https://cowengroup.com/

Never eat alone!

 

This one hits different.

David Cowen sits down with legal operations leader Carl Morrison (Otsuka Pharmaceuticals) for a sharp, high-energy conversation on how legal teams are turning data into strategy, and why now is the moment to clean house, ditch the ROT (redundant, obsolete, trivial), and drive real value.

Yes, we open with Lady Gaga, because transformation has a rhythm.
But what follows is a masterclass in Legal Data Intelligence (LDI) and the future of legal operations.

In this episode:

• Why your data is a goldmine, but only if you mine it right
• How AI is changing early case assessment and risk visibility
• What LDI really means, and why it’s not just about cost control anymore
• How legal ops teams are becoming strategic drivers, not just back-office fixers

Carl also shares what it means to move from dirty data to strategic sun, and how to build a cleaner, smarter, faster-functioning legal department in the age of AI and collaboration.

Whether you’re in legal ops, litigation, InfoGov, or leading a law department, this is your blueprint for going from now to next!

🎧 Subscribe on Apple Podcasts, Spotify, or wherever you listen. Don't forget to share this episode with your peers and colleagues.

💡To learn more about the future of legal innovation, visit https://cowengroup.com/

Never eat alone!

“Life is a carnival—and legal ops is leading the parade.”

What happens when strategy, storytelling, and AI collide in the hands of a legal operations leader? You get this high-energy, insight-rich episode with Elizabeth Lugones, VP of Professional Services at Mitratech, a legal tech pro who’s been writing and speaking about workforce automation since before it was cool.

What You’ll Hear:

• Why change management is really just executive storytelling
• How Sarah Sawvell at Honeywell, along with Mitratech and Morae, is crushing implementation through collaboration
• The shift from “cut costs” to “see around corners” in legal value
• How Liz and David use AI agents like ChatGPT + Gemini to create time dividends in real life
• Shoutouts to innovators like Stephanie Corey, Stacey Lettie, Anna Richards, Brittany Leonard, and more

If you’re leading transformation or trying to ride the wave, it’s time to rethink what legal value really means. Elizabeth brings the clarity. David brings the energy. And the future of legal just might be more human than ever.

🎧 Subscribe on Apple Podcasts, Spotify, or wherever you listen. Share this episode and take your career from now to next!

💡To learn more about the future of legal innovation, visit https://cowengroup.com/

Never eat alone!

 

What happens when three top legal innovators challenge everything we know about leadership, AI, and the future of law firms?

In this high-energy episode of Careers in the Business of Law, David Cowen sits down with three powerhouse legal minds who are redefining innovation, knowledge management, and practice transformation at major law firms. But here’s the twist—we’re not telling you who’s who right away!

Topics That Will Change How You Think About Legal Leadership:

• Who’s really driving innovation - clients or law firms?
• Why curiosity is more valuable than having all the answers.
• How AI is transforming legal work - but only if you ask the right questions.
• What top law firms are doing to stay ahead of the disruption curve.
• The "hidden ROI" of legal innovation (hint: it’s not just about saving time).

Connect with Our Experts & Learn More:
- Ilona Logvinova – Director of Practice Innovation at Cleary Gottlieb
- Esther Bowers – Chief Practice Innovation Officer at Honigman LLP
- Evan Shenkman – Chief Knowledge & Innovation Officer at Fisher Phillips

🎧 Don’t just stay informed—stay ahead! Listen now on Apple Podcasts, Spotify, or your favorite platform.

To learn more about the future of legal innovation, visit https://cowengroup.com/

Never eat alone!

 

Legal data isn’t just for eDiscovery anymore—it’s a strategic weapon.

AI-driven analytics are transforming legal teams into business intelligence powerhouses, helping HR, compliance, and cybersecurity teams solve problems faster than ever before.

In this episode, Benjamin Sexton (JND) shares:

• How AI is shifting legal work—are we saving time or just creating more high-value tasks? 
• Why legal teams are becoming the “calculators” of business intelligence
• How Walgreens and other companies use eDiscovery tools to solve compliance challenges in hours, not weeks 

If you're in eDiscovery, legal ops, or compliance, this episode will change how you think about legal data—and your career. 

🎧 Subscribe on Apple Podcasts, Spotify, or wherever you listen. Share this episode and take your career from now to next!

💡To learn more about the future of legal innovation, visit https://cowengroup.com/

Never eat alone!

 

The legal industry is facing its “Netflix vs. Blockbuster” moment. AI, automation, and alternative legal service providers (ALSPs) are rapidly reshaping how legal services are delivered, and the biggest question is: Who will adapt—and who will be left behind?

Roger Pilc leads a $600M+ division at Epiq, bringing experience from McKinsey, Booz Allen, CA Technologies, and Pitney Bowes. With insights from Satya Nadella’s vision on AI, Clayton Christensen’s The Innovator’s Dilemma, and leadership lessons from Peter Drucker, Adam Grant(Author of Think Again), and Daniel Pink(Author of Drive), Roger explains how ALSPs are positioned to disrupt legal in ways law firms and Big Four consultancies cannot.

In this episode, we explore how Legal Service Management mirrors IT’s digital transformation, why Zach Posner at TLTF is betting on AI-driven legal platforms, and how Nicole Giantonio and the team at Epiq are investing in tech that’s changing legal service delivery.

Key Takeaways You Can Use Today:

• Legal is facing a “Simultaneous Equation Problem.” GCs must manage rising litigation, regulatory complexity, and shrinking budgets—but traditional models no longer work.
• AI & ALSPs Are Changing Everything. Like Netflix disrupting Blockbuster, AI-powered legal service models are creating massive efficiencies for corporate legal teams.
• The 30% Rule: Leadership is Talent Spotting. Echoing Bill Gates, Steve Jobs, and Jack Welch, Roger spends 30% of his time recruiting and developing top talent—a critical strategy for legal leaders.

📢 If you’re in legal tech, legal ops, or law firm leadership—this episode is a must. Tag a colleague who should hear this!

🎧 Subscribe on Apple Podcasts, Spotify, or wherever you listen. Share this episode and take your career from now to next!

💡To learn more about the future of legal innovation, visit https://cowengroup.com/

Never eat alone! Join The Cowen Café. Stay connected. Stay ahead.

🎙 Host: David Cowen, President of The Cowen Group
👤 Guest: Karen Eber – TED Speaker, Leadership Consultant, Author of The Perfect Story

💡Why This Episode Matters?
Your data is airtight. Your argument is solid. So why isn’t leadership buying in?

Here’s the reality: Data doesn’t change behavior. Emotion does.

Today, I’m sitting down with Karen Eber, master storyteller and leadership strategist, to break down:

• Why storytelling—not just numbers—drives decisions in legal & tech
• The biggest mistake leaders make when trying to persuade & influence
• A simple 4-question framework to craft stories that move people

Want to drive AI adoption? Secure budget? Get leadership buy-in? This episode will change how you communicate—forever.

🎯Takeaways You Can Use Today:

• The 4 must-ask questions before making any pitch
• Why legal teams struggle with change—and how to fix it
• How to tailor your message to different audiences

Names & Books Mentioned in This Episode:

📖 Karen’s Book: The Perfect Story
📖 Carla Harris’ Expect to Win – A must-read on leadership & career growth
📖 Dale Carnegie’s How to Win Friends and Influence People – The power of connection & influence
📖 Jim Collins’ Good to Great – Why companies (and careers) succeed or fail

🎤 Karen’s TED Talk: How Your Brain Responds to Stories – Watch here
📝 Karen’s Blog: Actionable storytelling tips – Visit her website

🎧 Subscribe on Apple Podcasts, Spotify, or wherever you listen. Share this episode and take your career from now to next!

📢 Know someone struggling to get buy-in? Send them this episode!

💡 Want more insights on legal innovation? visit https://cowengroup.com/

🔥 Never eat alone. Join The Cowen Café. Stay connected. Stay ahead.

Ever wonder how to build a career worthy of a Lifetime Achievement Award? My latest guest, Jay Leib, has done exactly that—and he's here to share how.

From his early days in software sales at RTI, to leadership roles at EY, Relativity, NextLP, and now Reveal, Jay has built his career through radical curiosity, relentless networking, and entrepreneurial grit.

We cover Jay’s jungle gym-like career moves, why curiosity and communication matter more than certifications, and the hacks that helped him create lasting connections—from LinkedIn coffee meetings to mentorship lessons from VC icon Troy Henikoff.

🎧 Tune in for:

• Jay's entrepreneurial story of "cash in, cash out" (and how he learned to handle cash flow stress).
• How answering "rows and columns" in a job interview changed his life.
• Career-defining lessons from EY and Relativity, including the power of focus and punctuality.
• Networking pro tips (and how he credits career success to LinkedIn outreach).
• Jay’s weekend curiosity hacks: AI tools (ChatGPT, Claude, Gemini) and lifelong learning.

🎧 Subscribe on Apple Podcasts, Spotify, or wherever you listen. Share this episode and take your career from now to next!

💡To learn more about the future of legal innovation, visit https://cowengroup.com/

Legal teams aren’t just tracking data—they’re driving business decisions with it. Today, I sit down with Dave Bernstein, Executive Director, Analytics at Wells Fargo, to unpack the rise of Legal Data Intelligence (LDI) and why it’s changing everything.

Dave shares his unconventional path from 18 years in shipping to legal analytics, how he built a data-driven legal department alongside leaders like Kim Wolf, Edward L., and Tim Davenport, and why AI tools like Microsoft Copilot are set to revolutionize legal work.

💡 One Big Idea: The best legal ops teams don’t just analyze what happened—they predict what’s next.

🎯 What You’ll Learn in this episode:
✅ How Wells Fargo built a high-impact legal data intelligence team
✅ The must-have skills for legal ops professionals (from meta-skills research by Julia Hasenzahl & Brian Meegan at ProSearch)
✅ Why AI won’t replace legal teams—but will replace the ones who don’t adapt (Microsoft Copilot is a game-changer)
✅ The truth about talent transformation—who thrives, who doesn’t, and why (Farrah Pepper & Adam Rouse are leading the way)
✅ The future of legal ops roles (Chief Legal Data Intelligence Officers are on the rise)

📚 Books Mentioned
📖 Be Data Analytical – Jordan Morrow
📖 Be Data Literate – Jordan Morrow

🚀 What’s Next? Meet Dave in Person
Join Dave Bernstein at SOLID Atlanta (Nov 4, 2025) alongside Kim Wolf, Farrah Pepper, and other legal ops leaders as they shape the future of LDI.

🔗 Register for SOLID Atlanta → https://solid.legal/solid-atlanta-2025/

🎧 Subscribe on Apple Podcasts, Spotify, or wherever you listen. Share this episode and take your career from now to next!

💡To learn more about the future of legal innovation, visit https://cowengroup.com/

Legal work isn’t just about managing data—it’s about unlocking intelligence. AI, eDiscovery, and Legal Data Intelligence (LDI) are transforming how firms analyze, predict, and strategize. Are you keeping up?

In this episode, Robert Keeling (Partner, Redgrave LLP) joins David Cowen to unpack how AI, legal data intelligence, and next-gen eDiscovery are transforming the legal industry.

🔹 From Paper to AI: How legal data moved from printed emails to Slack, chat, and AI-powered discovery.
🔹 The AI-Powered Law Firm: Will firms create AI associates like Goldman Sachs?
🔹 Legal Work in 2025: AI isn’t replacing lawyers—it’s changing who does what and how.
🔹 The AI Dividend: How AI is helping legal teams work smarter, reduce stress, and focus on strategy.
🔹 Order to Chaos: How Legal Data Intelligence (LDI) is bringing structure to the AI revolution.

🔔 Tap play now to future-proof your legal career—or risk falling behind.

💡To learn more about the future of legal innovation, visit https://cowengroup.com/

📢 The legal industry is at a tipping point. Are you ready? In this episode, David Cowen sits down with Ted Theodoropoulos, Founder & CEO of InfoDash, to unpack the biggest shifts redefining law firms, legal tech, and knowledge management.

From AI-powered legal services to the VC-style approach to tech investment, this conversation is packed with insights that will help you future-proof your career and your firm.

🔥 What You’ll Learn:
✅ The AI Wake-Up Call: How AI is pushing law firms to rethink innovation, risk, and business models
✅ Beyond Billable Hours: Why firms are shifting from revenue growth to margin expansion and efficiency
✅ The VC Playbook for Law Firms: How firms like Paul Hastings, Sullivan & Cromwell, and Seyfarth Shaw are investing in legal tech startups
✅ KM as a Profit Center: How Ogletree Deakins turned knowledge management into a seven-figure revenue stream
✅ Who’s Leading the Charge? Why firms like Wilson Sonsini (Neuron) and Cooley (Cooley Go) are redefining how legal services are delivered
✅ Career Acceleration: Why lifelong learning, adaptability, and intellectual horsepower are now table stakes

🎯 Who Should Listen?

• KM, Legal Ops, eDiscovery & AI Leaders looking to stay ahead of the curve
• Lawyers & Legal Professionals navigating tech disruption
• Legal Tech Founders & Entrepreneurs building the next big thing
• Anyone interested in how law firms are evolving in the AI era

🔗  Legal Innovation & KM Leaders Mentioned:
🔹 Joe Green (Chief Innovation Officer, Gunderson Dettmer)
🔹 Esther Bowers (KM & Innovation Expert)
🔹 Ed Macnamara (Chief Innovation Officer, ArentFox Schiff)
🔹 Wendy Curtis (Chief Innovation Officer, Orrick)
🔹 Lorie Almon (Chair and Managing Partner, Seyfarth Shaw)

📚 Books Mentioned:
📖 Legal Upheaval by Michele Destefano
📖 The Leader Upheaval Handbook by Michele Destefano
📖 Innovation in Law Firms: Implementing Successful Projects by Stuart Whittle & Catriona Wolfenden

📅 Join the Conversation:
🔥 The Cowen Café – Weekly roundtables on AI, legal careers & innovation
🎤 Legal Week NYC – Meet David & Ted in person at the industry’s biggest event

🎧 Subscribe, Rate & Share!
If this episode sparked new ideas, subscribe, review, and share with your network.

📍 Apple Podcasts | Spotify 

And remember: Never eat alone. 🚀

#LegalTech #KM #Innovation #FutureOfLaw #AI #LegalOperations #LawFirmLeadership

In this episode, David Cowen sits down with Nicole Giantonio, SVP and Chief Marketing Officer at Epiq, to explore how cutting-edge AI technology, bold investments, and strategic talent development are revolutionizing the legal industry. From Epiq’s game-changing AI Labs to Nicole’s private equity perspective on innovation, this conversation is a masterclass for anyone navigating the evolving world of legal services.

If you’re ready to future-proof your career and understand the forces shaping the next decade of law, this episode is your roadmap.

What’s Inside?

The Talent Shift: Nicole shares how AI is reshaping roles, creating higher-level opportunities, and why training with AI tools is non-negotiable for today’s professionals.

Boardroom Trends: Why Fortune 500 companies and Global 1000 law firms are making massive investments in legal tech—even without a clear ROI.

The Iceberg Effect: Nicole’s analogy explains the hidden creativity and acceleration beneath the surface of the legal industry—and why it’s gaining momentum.

Future of Legal Ops: Get a sneak peek into emerging trends like legal data intelligence, the role of agentic AI models, and how Epic is positioning itself for long-term innovation.

🎧 Love what you heard? Don’t forget to like, share, and subscribe to Careers in the Business of Law on Apple Podcasts, Spotify, or wherever you get your shows. Let’s take your career from now to next. And remember—never eat alone.

Episode Description:
In this episode, David Cowen speaks with Bobby Malhotra, Partner at Winston & Strawn and a founding member of Legal Data Intelligence (LDI). Together, they explore how AI, eDiscovery, and data governance are reshaping the legal industry. Bobby also highlights the power of mentorship, the evolution of legal data intelligence, and the lessons he’s learned from his own career journey. If you’re navigating the future of law, this conversation is a must-listen.

What’s Inside?

• eDiscovery’s Next Chapter: Bobby dives into how the field has evolved from email production to a sophisticated practice that influences case outcomes and strategies.
• The Role of AI in Legal Data: Discover how conversational AI is eliminating friction, accelerating time to insights, and revolutionizing how legal teams manage data.
• Legal Data Intelligence (LDI): Learn about the founding and mission of LDI, a professional network designed to tackle the most complex data challenges across disputes, transactions, and compliance.
• Mentorship and Leadership: Bobby shares how mentorship transformed his career and why building relationships with mentors and mentees is critical to success in the legal profession.
• Going Above and Beyond: Bobby recommends Unreasonable Hospitality by Will Guidara as a blueprint for creating extraordinary client experiences.

Key Mentions:

• Books: Unreasonable Hospitality by Will Guidara
• Influencers: Kathleen McDowell, John Rosenthal, and Scott Cohen
• Organizations: Legal Data Intelligence (LDI), and  Winston & Strawn

Takeaways

• Leverage AI Tools: Start using conversational AI like ChatGPT to interrogate your data and uncover insights faster.
• Mentorship Matters: Find mentors who align with your goals and reciprocate by sharing your own expertise.
• Join Professional Networks: Get involved with groups like LDI to connect with industry leaders and stay ahead of emerging trends.

🎧 Subscribe on Apple Podcasts, Spotify, or wherever you listen. Share this episode and take your career from now to next!

In this episode, David Cowen dives into the transformative role of Legal Data Intelligence (LDI) with industry leaders Julia Hasenzahl, Jeremiah Weasenforth, and Ashley Christakis. They discuss how meta-skills like strategic thinking and adaptability are reshaping legal operations and explore how experiential knowledge is driving predictive insights across the legal ecosystem.

Key Topics:

• Meta-Skills Matter: Why adaptability, curiosity, and problem-spotting are essential for thriving in LDI.
• Expanding Roles: How LDI professionals are integrating e-discovery, governance, privacy, and risk management.
• Building Talent: The importance of fostering a culture of radical thinking to attract top talent in a competitive market.
• Better vs. Different: The dual need to improve current processes while rethinking how legal data is used to create predictive strategies.

Meet the Guests:

• Julia Hasenzahl : Co-founder and CEO of ProSearch, a leader in applying data intelligence to legal operations and e-discovery.
• Jeremiah Weasenforth: Legal Analytics Director at Edward Jones, pioneering data-driven approaches to legal strategy.
• Ashley Christakis: Senior Manager eDiscovery and Legal Operations at CrowdStrike, innovating the intersection of e-discovery and operational excellence.

Subscribe and Share:
Catch every episode of Careers in the Business of Law on Apple Podcasts, Spotify, or wherever you listen.
Take your career from now to next. Never eat alone.

In this episode, David Cowen chats with Kevin Cohn, Chief Customer Officer at Brightflag, about how next-gen technology and AI are reshaping legal operations, the war for talent, and the evolving role of legal professionals. If you’re navigating the future of law, this conversation is your roadmap.

What’s Inside?

• Brightflag’s Impact: Learn how Brightflag uses AI to transform legal billing and matter management for clients like Spotify and SAP, enabling legal teams to shift from admin to strategy.
• Tech & Talent Arms Race: Why GCs are hiring legal ops pros first and how AI is disrupting lower-level work while increasing demand for top talent.
• OKRs in Action: Kevin shares insights from Measure What Matters by John Doerr and how OKRs drive long-term innovation at Brightflag.
• Future-Proofing Your Career: Why training with AI tools like ChatGPT is critical to stay competitive in 2025 and beyond.

Key Mentions -

• Books: Measure What Matters by John Doerr
• Influencers: Tomasz Tunguz, Dave Kellogg, Daniel Young (Shark Ninja), Eva Bogucki (Cargill).
• Podcasts: Brightflag’s legal ops podcast hosted by Alex Kelly.

Takeaways -

• Train with AI: Spend an hour a day with tools like ChatGPT or Gemini to stay ahead.
• Build Your Network: Surround yourself with thinkers and tech leaders to sharpen your career edge.
• Think Long-Term: Apply OKRs to stretch your goals and align them with future trends.

Quotes -

• "If you’re not training with AI, you’re falling behind." – Kevin Cohn
• "Your career is a jungle gym, not a ladder—never eat alone and think out loud with others." – David Cowen

🎧 Subscribe on Apple Podcasts, Spotify, or wherever you listen. Share this episode and take your career from now to next!

Join us as we sit down with Zach Posner, founder of The Legal Tech Fund (TLTF) and the visionary behind the TLTF Summit, to unpack the unprecedented surge of innovation, talent, and investment reshaping the legal industry. From the rise of generative AI to law firms embracing venture capital mindsets, Zach offers insider insights into where legal tech is headed and why now is the time to lean in.

What You’ll Learn in This Episode:

• The $1 Billion Day in Legal Tech: How a single day in 2024 redefined the investment landscape.
• Generative AI’s Legal Impact: The explosion of generative AI startups and what it means for law firms and legal operations.
• Legal Tech’s Talent Revolution: Why top talent from Google, Facebook, and Netflix is flocking to legal tech startups.
• The Pyramid of Legal Tech Growth: Breaking down the lifecycle of startups—from early-stage experiments to scalable success.
• Law Firms as VCs: How firms are experimenting with technology and funding innovation to future-proof their practices.
• Retention Through Innovation: Why firms investing in cutting-edge tech are winning the war for talent.

Key Highlights:

• (1:08) ChatGPT’s historic debut and its role in igniting a generative AI gold rush.
• (3:28) The 239% growth in generative AI startups in just eight months—what’s driving this explosive trend.
• (12:13) Why law firms with innovation funds are attracting and retaining top talent.
• (14:17) The Rubik’s Cube analogy: How law firms are experimenting with tech to find the perfect fit.
• (15:03) The importance of focusing tech adoption in high-impact practice areas for maximum ROI.

Connect with Zach Posner:
LinkedIn: Zach Posner

Subscribe and Share:
Don’t miss an episode—find us on Apple Podcasts, Spotify, or your favorite platform. If you’re ready to take your career from now to next, remember: never eat alone.

Join us as we sit down with Paula Reichenberg, founder of NEUR.ON, a groundbreaking legal tech startup addressing multilingual challenges in the legal industry. Paula shares her entrepreneurial journey, from managing her family’s wine business at 16 to stepping onto the TLTF startup stage, and her mission to take NEUR.ON global.

What You’ll Learn in This Episode:

• From Law to Leadership: How Paula’s legal career inspired her to become a founder and solve real-world problems.
• The Power of Pivoting: How a client’s request for translations revealed a massive market opportunity.
• Building NEUR.ON: The story behind the name and how clever branding plays a pivotal role in startup success.
• The Multilingual Legal Challenge: Insights into the critical role of language in global legal operations.
• What’s Next for NEUR.ON: Plans to expand to the US and UK, with a bold vision for growth over the next 12 months.

Connect with Paula Reichenberg:

• LinkedIn: Paula Reichenberg
• NEUR.ON

Subscribe and Share: Don’t miss an episode—find us on Apple Podcasts, Spotify, or your favorite platform.

Take your career from now to next. Never eat alone.

In this episode, Brian Liu, co-founder of LegalZoom and founder of Overture Law, shares his journey of building not one, but two game-changing legal tech companies. After a wildly successful exit from LegalZoom, Brian dives back into the entrepreneurial world with Overture Law, a platform transforming how attorneys refer clients and share fees—ethically and efficiently.

Key Topics:

• LegalZoom’s Legacy and Lessons:
  • Founding LegalZoom in 1999 and leading it to public success in 2021.
  • Reflections on the challenges of building a legal tech pioneer.
• The Spark Behind Overture Law:
  • Identifying a gap in attorney referrals for non-contingency cases.
  • Creating a platform where attorneys can ethically refer clients and share fees, leveraging innovative technology to streamline connections.
• How Overture Works:
  • Combining LinkedIn, Yelp, and Match.com for attorney referrals.
  • Utilizing generative AI to enhance profiles and aggregating ratings for transparency.
• Building a Second Startup:
  • Recruiting co-founders and developing a minimum viable product (MVP) in four months.
  • Growing the network to over 5,000 attorneys, adding hundreds weekly.

Resources Mentioned:

• Explore Overture Law: Overture.law
• LinkedIn: Brian Liu

Memorable Quote:

"Don’t tackle everything at once. Find one small niche, one customer need, and attack it. You’ll be surprised how big it can become." – Brian Liu

If you’re a founder or legal tech innovator, this episode is packed with inspiration and practical advice.

Subscribe and share on Apple Podcasts, Spotify, or wherever you listen to your shows.

Take your career from now to next. Never eat alone.

In this episode, Crispin Passmore, a leading voice in legal innovation, unpacks the transformative potential of Alternative Business Structures (ABS), famously pioneered in Arizona. With a rich background as a regulator and policy expert in England and Wales, Crispin brings a unique perspective on how changes in ownership rules are reshaping the legal market globally.

Key Topics:

• What is the Arizona Model? How Arizona has opened the door for non-lawyers to own and invest in law firms, following a decade of success in England and Wales.
• Impact on the Legal Market: The ripple effects of ABS on legal innovation, client choices, and competition, from individual consumers to global corporations.
• The Economics of Change: Why external capital creates opportunities for long-term growth and innovation that traditional partnership models can’t sustain.
• The Role of Regulation: How regulators can balance modernization with oversight and why failing to adapt will result in market-driven change.

Resources Mentioned:

• LinkedIn: Crispin Passmore
• Book Mentioned: Another Country by James Baldwin

Memorable Quote:

"If you free up markets, they grow. Liberalization helps meet the needs of 100% of legal consumers, not just 20%." – Crispin Passmore

If you enjoyed this episode, subscribe and leave a review on Apple Podcasts or Spotify.

Take your career from now to next. Never eat alone.

In this episode, we sit down with Ned Gannon, the visionary founder of Coheso and previously eBrevia, to unpack his 14-year journey in the evolving legal tech landscape. As a second-time founder with a proven track record, Ned shares unique insights into the challenges and opportunities of building AI-driven solutions for the legal industry. From scaling eBrevia to its successful exit, to the launch of Coheso, Ned is a seasoned voice in how innovation is reshaping law.

What You’ll Learn in This Episode:

• A Tale of Two Startups: Explore the early days of eBrevia (2011–2012) and how the legal tech landscape has matured since then, creating a more dynamic, fast-paced environment for founders today.
• The Origin of Coheso: Learn how Ned and his co-founders, AI engineers from Carnegie Mellon, are bridging the gap between business and legal teams with a cutting-edge platform designed to manage legal requests, automate routine processes, and prioritize work.
• Market Maturity and Acceleration: Ned reflects on how funding, buyer sophistication, and talent pools in legal tech have quadrupled over the past decade, leading to faster innovation cycles.
• Insights for Founders:
  - The importance of talent spotting and talent slotting in building a successful team.
  - The role of iteration and client feedback in scaling products quickly.
  - Lessons from managing risk capital and limiting dilution to set startups on a trajectory for success.
• Ned’s Day-to-Day: What life as a legal tech founder looks like, from onboarding large clients to iterating on features in response to customer needs.

Connect with Ned and Coheso:

• Website: Coheso
• LinkedIn: Ned Gannon

For Founders, By Founders:
If you’re an entrepreneur in legal tech or just curious about the space, this episode provides a masterclass on building and scaling AI-driven solutions in an increasingly dynamic market.

If you enjoyed this conversation, subscribe and leave a review on Apple Podcasts, Spotify, or wherever you get your shows. Let’s take your career from now to next.

Never eat alone.

In this episode, we shine a spotlight on Katon Luaces, one of the youngest founders at TLTF 2024. At just 25 years old, Katon took the Startup Stage by storm, presenting his company PointOne to a packed room of investors, customers, and industry leaders. PointOne is revolutionizing the legal industry with its cutting-edge automated time-tracking solution for attorneys, helping them focus on practicing law, not tracking hours.

What You’ll Hear in This Episode:

• Startup Stage Reflections: Katon shares what it’s like to pitch in front of 200+ stakeholders at TLTF and offers advice for future founders.
• PointOne’s Origin Story: Discover how Katon’s co-founder, an ex-corporate attorney frustrated with time tracking, inspired the creation of PointOne.
• Magic of Automation: Learn how PointOne uses generative AI and large language models to seamlessly track lawyers’ work in six-minute increments—no interruptions or manual input required.
• From Google Intern to Founder: Hear about Katon’s journey, starting with a gritty self-taught coding effort that led to a freshman-year internship at Google.
• Insights on Building a Team: With co-founders Jeremy Ben-Meir and Adrian Parlow, PointOne is bridging the gap between tech and law, solving real problems with innovative solutions.

Why Listen?
Katon’s story is a testament to grit, adaptability, and innovation. Whether you're an aspiring entrepreneur, a legal professional, or just curious about how the next generation is solving age-old industry challenges, this episode is for you.

Connect with Katon and PointOne:
Website: PointOne
LinkedIn: Katon Luaces

If you enjoyed this episode, don’t forget to like, share, and subscribe on Apple Podcasts, Spotify, or wherever you get your shows. Let’s take your career from now to next.

Never eat alone.

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!

🎙️ Discover the Power of Legal Data Intelligence! Join David Cowen as he sits down with Alison Grounds, Partner & Managing Director of Troutman Pepper eMerge, for a deep dive into the evolving world of legal data intelligence. From curating the e-discovery process to shaping the future of data governance, Alison shares insights on how this space is transforming and creating new opportunities for legal professionals.

🔥 Episode Highlights:

• Curious & Evangelizing LDI: Alison talks about her journey into Legal Data Intelligence, noting how she’s both "curious and an evangelist" for this growing field, driven by the need to manage legal information intelligently.
• Sun and ROT Explained: Alison unpacks the concept of "sun and rot" — where sun represents valuable, actionable data, and ROT refers to redundant, obsolete, and trivial information that clogs the system.
• Proactive Legal Strategies: With a focus on proactive client strategies, Alison discusses how 70% of her current work is spent on forward-thinking data governance and litigation readiness, a shift from reactive e-discovery.

🚀 Special Mentions:

• Listen to Alison Grounds previous podcast with David Cowen - Click here
• Briordy Meyers - to know more about him listen his podcast here
• Scott Milner - to know more about him listen his podcast here
• Bill Potter - LinkedIn

🎧 Tune in Now! Whether you’re new to legal data intelligence or a seasoned professional, this episode is packed with actionable insights. Learn how data is driving new methodologies, creating proactive legal strategies, and offering fresh career opportunities. Plus, get Alison’s playlist recommendation featuring Leon Bridges!

🎙️ Unlock the Future of Legal Tech! Join David Cowen as he talks with Marla Crawford, General Counsel at Cimplifi, in this dynamic episode of "Legal Data Intelligence Series." Dive into Marla's journey from Jones Day to Goldman Sachs, where she stood up their eDiscovery group, to her current work at Cimplifi. Marla shares invaluable insights on how data intelligence is transforming the legal industry and shaping new career paths.

🔥 Episode Highlights:

• Building eDiscovery from Scratch: Marla reflects on her early days at Goldman Sachs, where she had “a lot of freedom” to create their eDiscovery program and how it shaped her career.
• Legal Data Intelligence’s Impact: Today, Marla is driving innovations in data intelligence, sharing that “the power of data is limitless” and opening up exciting opportunities in the legal field.
• Corporate Legal’s New Role: Marla explains how corporate legal departments are evolving, becoming more than just a “cost center” and instead, key players in driving business value through technology.

🚀 Special Mentions:

• Marla Crawford, Cimplifi
• Goldman Sachs
• Jones Day

🎧 Tune in Now! Whether you're a seasoned professional or new to the field, this episode is packed with fascinating stories and actionable insights into how legal data intelligence is changing the way legal departments operate. You won't want to miss Marla’s expert take on the intersection of law, data, and technology.

 

🎙️ Explore the Evolution of Legal Tech! Join David Cowen as he sits down with Daniel Gold, a legal tech pioneer currently leading at BDO, in this insightful episode of "Legal Data Intelligence Series." Dive into Daniel’s journey from law school to becoming a key player in the e-discovery space, and learn how community and innovation drive the industry forward.

🔥 Episode Highlights:

• From Law Firm to Legal Tech Leader: Daniel recounts his early days in a small law firm, where he transitioned from traditional legal practices to embracing e-discovery and legal technology.
• Building a Community in Legal Tech: Discover how Daniel views LDI (Legal Data Intelligence) as more than just a model—it's a thriving community that fosters collaboration and innovation.
• The Role of Generative AI: Daniel shares insights on the growing demand for AI expertise, emphasizing the importance of prompt engineering and its impact on the legal field.

🚀 Special Mentions:

• Daniel Gold - LinkedIn Profile
• BDO - BDO USA
• George Socha - LinkedIn Profile
• Andrew Seija - LinkedIn Profile
• Nick Robertson - LinkedIn Profile
• Adi Elliot - LinkedIn Profile
• Major Baisden - LinkedIn Profile
• Chris Haley - LinkedIn Profile

🎧 Don’t Miss Out! This episode is filled with valuable insights, fascinating personal stories, and an in-depth look at the evolution of legal technology. Whether you're an industry veteran or just curious about the future of legal tech, Daniel's expertise and experience will leave you both informed and inspired.

Tune in now and discover how legal tech is shaping the future of law!

 

In this episode of "Careers in the Business of Law," part of the LDI Legal Data Intelligence Series, host David Cowen sits down with Scott Milner, Laura Kibbe, and Adam Rouse for a deep dive into the concept of Legal Data Intelligence (LDI). Recorded live from the ILTA conference in Nashville, this episode offers an engaging recap of their session on stage, discussing how LDI is transforming the legal industry.

🔥 Episode Highlights:

• Introduction to Legal Data Intelligence: Laura Kibbe kicks off the conversation by introducing the LDI model and framework, explaining how many legal professionals have unknowingly been practicing LDI for years. The team discusses the eye-opening moment for many attendees when they realized the value and breadth of the LDI community.

• The LDI Framework: Adam Rouse breaks down the LDI template, focusing on the "Initiate, Investigate, Implement" process. He shares insights on how this framework provides a blueprint for legal professionals, eliminating the need to start from scratch on new projects.

• Technology’s Dual Role: Scott Milner discusses how technology is both a challenge and a solution in managing the volume, variety, and velocity of data. He emphasizes how leveraging technology is crucial for legal professionals to keep pace with the accelerating demands of the industry.

• Shifting Legal Roles: The conversation highlights how the role of in-house legal departments is evolving from being a cost center to a strategic partner. Legal professionals are now expected to provide business insights and add value beyond traditional legal advice.

• Diversity in the LDI Community: The panel reflects on the diverse audience at ILTA, from young professionals to seasoned experts, all eager to leverage LDI in their careers. The discussion emphasizes the importance of fostering a community that supports career mobility and skill development.

🚀 Special Mentions:

• Scott Milner - LinkedIn
• Laura Kibbe - LinkedIn
• Adam Rouse - LinkedIn
• Legal Data Intelligence - Website
• ILTA (International Legal Technology Association) - Website

🎧 Tune In Now!

Whether you're new to LDI or a seasoned professional, this episode is packed with actionable insights and expert advice on how Legal Data Intelligence is reshaping the legal landscape. Join the conversation and learn how you can leverage LDI to accelerate your career and add value to your organization.