Careers and the Business of Law

Mary Agbovi runs legal operations at CoverMyMeds, sits on the SOLID Advisory Council, and co-founded an organization that builds schools in Togo. David Cowen sits down with Mary to unpack the most quotable metaphor in the entire series: what if we had given Alexander Hamilton a typewriter? It is a reframing of change management that strips away the fear of AI replacement and replaces it with something more useful, we are handing our teams tools to be more of who they already are. Key Topics Covered:

• The Hamilton typewriter metaphor: Why we are giving people an amplifier, not asking them to change identity
• Concentric circles of AI rollout: Mary's framework for thinking about adoption — direct team first, then the surrounding stakeholders
• The bell curve of adoption: What to do with the leading 20 percent, the middle 60, and the trailing edge
• Building schools, building legal ops: Why creating space for people to learn is the same fundamental work
• Inspiring agency: Why storytelling is the differentiator for legal ops leaders in 2026
• Articulation as AI dividend: How Mary uses AI as a coach to refine her own thinking
• Project managing a life: Three daughters, building schools, leading legal ops

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💡To learn more about the future of legal innovation, visit https://solid.legal/podcasts/ Never eat alone!

Carl Morrison is the legal operations ambassador to Las Vegas, a CLOC board member, and one of the people who built the legal operations function on the Las Vegas Strip. David Cowen sits down with Carl to trace the evolution of legal ops from his first CLOC at the Bellagio a decade ago to today's McCormick Place, and to unpack the central question of this moment: are we using AI as a tool, or are we becoming enslaved to it? Key Topics Covered:

• The CLOC origin story: Building the first legal ops function in Las Vegas gaming and hospitality
• The CLOC 101 Academy: Why the entry-level program now serves over 150 attendees
• Slavery vs. freedom: Carl's framing of the choice every legal team faces with AI
• Personal agency as the answer: Why the automation question is fundamentally about who you want to be
• The Claude conversation: Why model preference shifts month to month and why the relationship matters more than the tool
• Fearlessness as career strategy: Why curiosity matters more than credentials

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💡To learn more about the future of legal innovation, visit https://solid.legal/podcasts/ Never eat alone!

Zach Posner sees more legal tech founders than almost anyone alive. As founder of The LegalTech Fund, his portfolio includes over 80 companies. David Cowen sits down with Zach, minutes after Anthropic dropped a major legal partnerships announcement, to unpack the macro view: where we are in the cycle, why talent demand is exploding rather than collapsing, and why the most valuable founders are the ones willing to pivot when the data tells them to. Key Topics Covered:

• Years happen in days: The investor's frame for the current pace of change
• The Anthropic announcement: Zach's real-time reaction to twenty-plus legal partnerships and the news that legal is Anthropic's most active power user vertical
• The trillion-dollar market: Why $300B sits in litigation (the loud part) and $700B in business-as-usual
• The talent surge nobody is reporting: Software engineer demand up 15.6 percent in twelve months
• The Pathways Project: Zach's initiative predicting what legal looks like in 2040
• Founders who pivot: Why none of the founders Zach meets are doing what they originally said they would
• TLTF in Scottsdale: Why November's invite-only gathering remains the Davos of legal tech

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💡To learn more about the future of legal innovation, visit https://solid.legal/podcasts/ Never eat alone!

Joe Stephens just helped close a 49-million-dollar raise at steno. He also became a sommelier on the side. David Cowen sits down with Joe, director of legal solutions, law school professor, and one of the most thoughtful voices in litigation technology, to ask the question that defines this moment: what would you not automate? The answer pulls in John Cage, Unreasonable Hospitality, and why curiosity may be the only truly un-automatable skill left. Key Topics Covered:

• Service vs. hospitality: The distinction that powers steno's brand and why feel beats commodity
• What Joe would not automate: Physical connection, hugging his kids, walking the dog
• John Cage's 4'33": Why four and a half minutes of silence is the hardest piece of music ever composed
• The sommelier hobby: How Joe spends part of his AI dividend on deep human pursuits
• Listening and curiosity: The two skills Joe tells his students matter more than any technical knowledge
• Voice to text vs. pen and paper: Why composing a prompt forces slow thinking
• Unreasonable hospitality: Why delivering experience — not service — is the central differentiator in legal tech

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💡To learn more about the future of legal innovation, visit https://solid.legal/podcasts/ Never eat alone!

Lawyers participate in the downside and never the upside, and Jason Barnwell argues that is the single most important thing about to change. David Cowen sits down with Jason, the former Microsoft GM and associate GC who now leads legal at Agiloft, to unpack why the GC role is being rewritten around upside risk, why contract intelligence is becoming business intelligence, and why the legal leaders selling signal back to the enterprise will earn a seat at the CFO's table. Key Topics Covered:

• Upside risk vs. downside risk: Why legal moves from brake to accelerator and what that changes
• Probabilistic practice: Accepting outcomes that are less than perfect to open the aperture on what legal can do at scale
• Contract intelligence as business intelligence: How aggregated contract data becomes a strategic asset
• The cut line: How budget conversations reward the best stories — and what legal needs to do to stay above the line
• Storytelling as leadership: Lessons from Microsoft legends Brad Smith, Neil Suggs, and Hossein Nowbar
• Selling signal back to the enterprise: Packaging contract data into predictive insights that earn legal upside participation
• Faster deals as legal's superpower: Why predictive contracting becomes the GC's new currency

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💡To learn more about the future of legal innovation, visit https://solid.legal/podcasts/ Never eat alone!

David Cowen and Ari Kaplan have known each other for twenty years - this is their first podcast together. It is one of the most candid conversations in the series. Ari shares the philosophy that has carried him through two decades at the highest levels of corporate legal, why the US mindset about reclaimed time is a problem worth confronting, and why the most important question of the next decade may be the one Zach Kass asked from the keynote stage. Key Topics Covered:

• The validation tax: Ari's framework for the time you spend verifying AI output
• The AI dividend, US edition: Why Americans fill saved time with more work and Europeans leave earlier
• Permission to stop: David's confession of guilt around saved time and how to reframe it
• The mentorship moat: Why a Stanford-style simulation program might out-train a senior partner
• What AI cannot touch: Why high-stakes corporate work still requires human judgment and network
• Legal as R&D center: Why legal departments are becoming the experimentation hubs of the modern enterprise
• The renaissance of legal: Why the energy on the CLOC floor in 2026 feels fundamentally different

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💡To learn more about the future of legal innovation, visit https://solid.legal/podcasts/ Never eat alone!

The most honest read on AI adoption in legal might be borrowed from Hemingway: slowly, and then all at once. David Cowen sits down with Adam Becker, director of legal operations at Cockroach Labs, CLOC board member, and one of the architects of the CLOC 101 Academy - to unpack what has actually changed in the last six months, why his team is no longer impressed by AI but expects it, and why the real question is what you are doing with the time AI gives you back. Key Topics Covered:

• Slowly, then all at once: Why the adoption curve follows the same pattern as every transformational technology before it
• Capability over efficiency: Why the most important AI gain is being able to do things you literally could not do before
• The talent surge thesis: Why legal hiring is about to grow, not contract
• Stratifying the legal stack: NDAs to contract managers, vendor agreements to agents, lawyers to high-stakes work
• Wordle as a discipline: Why the made bed and the cleaned kitchen are not small things
• The automated birthday message problem: What we should and should not delegate to our agents
• The AI dividend list: David's analog notebook of things to do with reclaimed time

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💡To learn more about the future of legal innovation, visit https://solid.legal/podcasts/ Never eat alone!

The pace of change in legal tech is no longer linear - it is exponential. David Cowen sits down with Colin Levy, one of legal tech's most prolific voices, to unpack why we are still at the frontier, why human appetite is failing to keep up with capability, and why daily discipline is the unsung superpower of every leader in this space. Key Topics Covered:

• Still at the frontier: Why the next five months will deliver more change than all of last year
• Appetite vs. capability: The widening gap between what AI can do and what humans can absorb
• The 5:30 AM discipline: Colin's daily writing practice and why a blank page is his most valuable tool
• Curiosity as a multiplier: Why the people winning right now read the technical guts of AI, not just the headlines
• The tipping point ahead: Colin's prediction that something big is coming — not a black swan, but a development beyond what anyone is imagining

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💡To learn more about the future of legal innovation, visit https://solid.legal/podcasts/ Never eat alone!

Legal tech used to live in the trunk - pulled out only when something broke. That era is over. David Cowen sits down with Chad Ergun, whose career has spanned Shearman & Sterling, White & Case, and Gibson Dunn before landing at Womble. Chad unpacks why mid-size firms are now competing with BigLaw, why his refusal to lock into a single AI vendor may be the smartest move in legal IT, and why simulation training is replacing the apprenticeship model.

Key Topics Covered:

• Legal tech's promotion: From the trunk to the passenger seat to the driver's seat
• The roofing contractor problem: Why the billable hour cannot survive predictable outcomes, timelines, and costs
• Model hopping as strategy: Why Chad runs six different AI models and refuses vendor lock-in
• Simulation training for associates: Borrowing from pilots and surgeons to fix the mentorship gap
• AI doesn't judge you: Why associates ask AI the questions they were too afraid to ask their partners
• Enterprise data sovereignty: Why running AI on your own tenant is non-negotiable
• The end of the billable hour by 2027: Chad weighs in on Anthropic GC's bold prediction

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💡To learn more about the future of legal innovation, visit https://solid.legal/podcasts/ Never eat alone!

In a market flooded with AI tools, the smartest legal teams aren't chasing technology first - they're slowing down to ask better questions. In this episode of Careers and the Business of Law, David Cowen sits down with Stacy Lettie, James Vinson, and Scott Milner to unpack why design thinking is making a comeback in the AI era. Special shoutout to Nitant Narang for jumping into the conversation and raising one of the most important questions of the episode: when does asking "why" become too much?

The conversation cuts through the hype around legal AI and focuses on something far more valuable: defining the right problem before rushing toward a solution. From practical frameworks to real-world failures, the panel explores how legal professionals can think more strategically, collaborate more effectively, and avoid wasting time and money on "shiny software" that doesn't solve the actual issue.

Key Topics Covered:

• Why most legal teams are moving too fast into AI adoption without defining the underlying business problem first
• The real meaning of design thinking - minus the consultant jargon and buzzwords
• How asking "Why?" repeatedly uncovers the actual issue hiding beneath the surface
• The shift from "technology first" back to "people, process, then technology"
• Why communities like Legal Data Intelligence help legal professionals solve problems faster and avoid reinventing the wheel
• The importance of prototyping, failing early, and learning through experimentation instead of chasing perfection
• Why the future value of legal professionals will come from asking the right questions - not just delivering answers

🎧 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://solid.legal/podcasts/ Never eat alone!