Podcast appearances and mentions of david cowen

Hosted by David Cowen | Careers and the Business of Law Fresh off four days at McCormick Place in Chicago, David Cowen sits down with Oyango Snell, President & CEO of CLOC, for a post-CGI debrief. The energy on the floor was unmistakable: this is not the same industry it was twelve months ago. From Second City opening every morning to standing-room-only sessions on AI maturity, CGI 2026 signaled that the legal ops community has moved from anxiety to confident curiosity. WHY THIS MATTERS The legal industry is no longer asking if AI matters. It's asking how to measure it. With budgets flat and demand rising, legal ops professionals are being forced to get strategic. This conversation captures the mood of the market and where the next five years are headed. KEY TAKEAWAYS Attendees came with hands-on experience and real questions. Anxiety is out, confident curiosity is in. Legal ops has moved from chaos to at least ad hoc, if not operational, on the maturity arc. "Do more with less" is hogwash. Flat budgets plus rising demand requires strategy, not just effort. AI won't replace jobs. People who leverage AI will replace those who don't. A growing economy means more demand for legal services. The doomsday narrative doesn't hold up. Education is the new currency. CLOC Academy is hitting the road to reach those who can't make it to CGI. Legal ops sits at the intersection of law and technology. That's the superpower. Own it. CGI 2027 is back at the Aria in Las Vegas. Pro tip from David: Thank the speakers. Easiest networking move there is. Pro tip from Oyango: Own your professional stake. Relationships are built through follow-up, not just introductions. PEOPLE MENTIONED David Cowen, Host Oyango Snell, President & CEO, CLOC Kevin Clem, Harbor; co-author of the State of the Industry Report Zach Kass, CGI 2026 Keynote Speaker Mary O'Connell, Market leader, referenced Connie Brenton, Founder and CEO, LegalOps.com COMPANIES & ORGANIZATIONS MENTIONED CLOC, Corporate Legal Operations Consortium; host of CGI and legal ops community anchor Harbor, Co-produced the 2026 State of the Industry Report with CLOC Second City, Opened each day of CGI 2026 and set the tone for the conference Anthropic, Ivo, OpenAI, Among the vendors actively hiring legal tech talent SOLID, Legal career and education community; Solid New York on October 1st CLOC Academy, Educational arm of CLOC, now going on the road beyond CGI

LexisNexis CEO of Global Legal Sean Fitzpatrick joins David Cowen to unpack the newly announced strategic alliance with Luminance and what it signals about where legal work is actually headed. From the "trust-first" shift replacing better-faster-cheaper, to law firms growing margins while raising rates, to the emergence of an entirely new role (manager of agents), this conversation is a candid read on how AI is reshaping the practice, the workflow, and the talent equation in legal. Key Topics Covered Why the LexisNexis and Luminance integration was customer-demanded, and how authoritative legal content plus contract intelligence changes the workflow equation ChatGPT as a step change, not an incremental shift: the strategy stayed the same, the tools changed everything The three buckets of legal work (repeatable/rules-based, judgment-based, and pure thought leadership) and where AI actually plays The "AI dividend" in practice: a GC reclaiming 10 hours a week to turn warranty claims from cost center into profit driver Why trust now outranks speed and cost as the dominant buying criterion in legal AI How law firms are growing revenue faster than cost base, and pushing high-single-digit rate increases The role that doesn't exist yet: manager of agents, leading a workforce with no human employees "AI fluidity" as the new hiring filter, plus career advice on reputation, partner selection, and taking risks early (with a Shoe Dog recommendation)

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

Kim Wolfe is one of the few non-lawyer executives running operations at the top of corporate legal. With a Wharton MBA and a quantitative background, she leads legal administration at State Street. David Cowen sits down with Kim to unpack what executive-level legal ops looks like inside one of the world's most regulated industries, and the career advice that changed everything. Key Topics Covered: The non-lawyer operator archetype: How business operators in legal leadership are reshaping the function Banking's slower AI path: Why regulation means Kim is two steps behind Intel and HP, and okay with that Lawyer-to-lawyer training: Why pairing power users with hesitant adopters moves the needle Who owns training: Why 67 percent of legal ops says it belongs to them The career lesson: As long as I see you here, I cannot give you more The 5:30 AM discipline: Why two hours of solo thinking is Kim's most important investment Simulation training: Why flight-simulator-style learning may fix inconsistent mentorship

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

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

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

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

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

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

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

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

The legal department has spent decades as a reactive cost center, called in to fix problems, not prevent them. That's over. In this conversation recorded live at the UDF Lighthouse Customer Forum in Scottsdale, David Cowen sits down with Russ Elmer, General Counsel of ServiceNow, to unpack why 2026 is the year legal transforms from bottleneck to force multiplier, and why the CLO's team is uniquely positioned to become the strategic hub of the entire enterprise. Key Topics Covered: Legal as the enterprise hub: Why the legal department, which touches HR, engineering, finance, and beyond, is better positioned than any other function to generate cross-functional intelligence at scale The bundling/unbundling inflection point: Law firms spent 40 years bundling every knowledge service imaginable. AI is now unbundling all of it, and what's left (judgment, context, relationships) is exactly where great lawyers live The AI dividend: When routine questions and contract redlines get automated, an entire workforce of critically-trained, liberal arts-educated thinkers gets unchained from their desks and unleashed on strategic problems The digital twin concept: Russ shares his vision for a "smarter Russ Elmer," an AI that doesn't just replicate his decisions, but improves on them in real time Brain + arms and legs: Why information alone is worthless without action, and how the ServiceNow partnership is designed to close that gap from insight to outcome The forward-deployed legal engineer: David's framework for the most important career move in legal right now: embed, bridge, build, and grind, because 2026 is the year you either double down or fall behind What legal looks like in 2030: How Russ's team is reimagining org structure, work distribution, and the very definition of what a legal job is  

Live from Legalweek 2026, David Cowen sits down with Evan Wong, co-founder and CEO of Checkbox, to unpack a problem most legal teams still haven't solved: legal has software, but it still doesn't have a true operating system. This episode gets into why intake remains broken, why legal ops is becoming one of the most important roles in the business of law, and why the next wave of AI value will come from embedding legal into the tools the business already uses. Hosted by David Cowen Key Topics Covered Why Evan built Checkbox to become the operating system for legal, not just another point solution The core problem Checkbox solves: legal intake is still messy, manual, and invisible across most organizations Why the first major champions of this category were legal ops leaders who understood legal as a business function How Checkbox evolved from a no-code workflow tool into a system of record and front door for legal Why the future of legal intake is not forms and ticketing systems, but AI embedded into email, Slack, Teams, Salesforce, and everyday workflows Evan's view that the GC is increasingly a wartime role, creating space for legal ops to evolve into a more strategic chief-level business function A hard truth about the market right now: the biggest challenge is not lack of tools, but too much noise, too many AI labels, and not enough clarity on what to implement first

Live from Legalweek 2026, David Cowen sits down with Curt Sigfstead, CFO of Clio, to unpack how one of legal tech's longest-running companies is moving upmarket and redefining what AI should do inside legal operations. The conversation centers on a major shift now underway: from software that assists lawyers to AI-powered teammates that qualify leads, streamline operations, and help law firms and legal departments rethink the way legal work actually gets done. Hosted by David Cowen Key Topics Covered Why Clio's origin story matters now: a company built for the cloud in 2008 is using that long-view advantage to enter the enterprise market at the right moment How Clio grew from serving solo and small firms to supporting a massive global footprint with 400,000 users across 130 countries Why the next legal AI opportunity is not just better research or drafting, but connecting legal work with the operational systems around it Clio's core argument for the future: AI should not just assist lawyers, it should perform tasks and move work forward A real example of AI in action: using AI to intake leads, qualify them, check conflicts, summarize issues, and save attorneys hours before the first call Why Kirk believes today's fragmented categories - research, document management, and AI tools - will eventually collapse into a more unified legal workflow The enterprise pitch: large law firms and corporate legal departments need partners who understand both the practice of law and the operations of legal service delivery

Recorded live from Legalweek, David Cowen sits down with Patrick Forquer, the CRO of Legora, to unpack what happens after the AI experimentation phase ends. The legal industry is shifting from curiosity to proof, where firms and corporate teams are demanding measurable ROI, faster workflows, and real business impact. The big takeaway: the real AI dividend isn't just saving time - it's accelerating work, improving outcomes, and unlocking revenue that used to sit trapped inside slow legal processes. Hosted by David Cowen Key Topics Covered Why legal AI has moved from experimentation to social proof, with firms now demanding measurable ROI instead of demos and hype The three layers of the AI dividend: saving time and cost, increasing the quantity and quality of work, and ultimately generating new revenue How faster contract cycles can unlock enterprise value by accelerating revenue rather than just reducing legal spend Why the smartest buyers cut through market noise and choose AI tools based on workflow fit and adoption readiness The new implementation reality: AI success requires post-sale enablement, legal engineers, and real operational change Why AI adoption is now a cross-functional decision involving leadership, innovation teams, knowledge management, and practitioners The talent shift underway as firms look for professionals who can bridge legal expertise with AI-driven execution

Live from Legalweek 2026, David Cowen sits down with Rian Kennedy, Director of Legal Hold Sales at DISCO, to talk about what has actually changed in legal tech over the last 12 months. The conversation goes beyond AI hype and gets into what matters now: cloud maturity, agentic workflows, insourcing pressure, tighter budgets, and why legal teams are starting to use technology to control spend, consolidate systems, and rethink where legal ops ends and business ops begins. Hosted by David Cowen Key Topics Covered Why the legal market has moved from cautious curiosity to real AI adoption, with law finally pushing to stay competitive instead of lagging behind How the pandemic accelerated cloud adoption and set the stage for today's faster embrace of GenAI and agentic AI Why the most valuable buyers are still the innovators who want to build alongside vendors before tools become table stakes How corporate legal teams are reassessing what to keep in-house, what to send to outside counsel, and where ALSPs fit in the middle Why legal ops leaders who mastered contracts and workflow discipline are now asking the bigger question: what comes next How litigation budgets are becoming a strategic focus, with more interest in visibility, control, consolidation, and reducing outside counsel spend Why legal hold, eDiscovery, and preservation are becoming more important as data sources multiply and automation becomes essential

Live from Legalweek 2026, David Cowen sits down with Rhys Hodkinson, CRO of Definely, to explore where legal AI gets truly useful for transactional lawyers. This episode is about moving beyond generic speed gains and into something more valuable: systems that understand contracts, surface the right context at the right moment, and help lawyers think more strategically without sacrificing precision or professional judgment. Hosted by David Cowen Key Topics Covered Why Definely was built to solve a problem most legal tech ignored: helping transactional lawyers work inside long, complex contracts where context is everything How Definely surfaces definitions, cross-references, schedules, annexes, and related documents directly inside Microsoft Word Why the real moat in legal AI is not just the model, but the grounding layer that understands how contracts actually work How prior contracts, past definitions, and historical drafting patterns can turn AI from a generic tool into a true drafting ally Why firms are under pressure to move faster with AI while still carrying the same professional liability for the final output Rhys's view that the market still has not figured out what to do with the AI dividend, even as lawyers gain speed, capability, and better output Why the next legal tech battle may be about interface and control: who becomes the layer where lawyers actually work, while specialized tools plug in behind the scenes

Live from Legalweek 2026, David Cowen sits down with Alex Smyth, EVP and General Counsel at LexisNexis, to talk about where legal AI is finally getting real. The industry is moving past one-off experiments and into repeatable workflows that cut turnaround times, reduce manual work, and deliver answers lawyers can actually trust. The big question now is no longer whether to use AI. It's how to embed it into legal work in a way that is authoritative, scalable, and measurable. Hosted by David Cowen Key Topics Covered Why the legal market is shifting from AI experimentation to repeatable workflows that automate entire sequences of work How LexisNexis built an NDA workflow that reviews, comments, escalates when needed, drafts the response email, and cuts review time from days to minutes A measurable legal ops outcome: LexisNexis reduced contract turnaround time in tracked segments by 22.7% over the last year Why nearly 300 legal workflows matter more than generic prompting, especially when lawyers need structured, repeatable outcomes The difference between general-purpose AI and purpose-built legal AI grounded in authoritative, curated legal content Why authoritative content still matters: lawyers need current law, validated citations, and trusted outputs, not just plausible answers Alex's view that the market is at an inflection point, where the real return on AI will come from embedding workflows directly into legal process

Live from Legalweek 2026, David Cowen sits down with Dennis Garcia, Vice President and General Counsel of Litera, to unpack what legal leaders still get wrong about AI, networking, and business impact. This episode is really about leverage: how trust, responsiveness, relationship-building, and smarter risk-taking turn legal from a support function into a revenue driver. Hosted by David Cowen Key Topics Covered: Why your network is still your net worth, and why LinkedIn remains one of the most underused career assets in law How commenting consistently on LinkedIn can build visibility, credibility, and real-world opportunities over time What Dennis learned moving from Microsoft to Litera, and why earning trust starts with responsiveness and clarity Why legal departments should stop being the department of no and start becoming business enablers How faster contract cycles drive revenue, margin, and growth by shrinking time to deal Why smaller legal teams need to be scrappy, versatile, and fluent in legal ops, AI, and business priorities The real future of legal work: combining human intelligence and AI to build trust, close deals, and move the business forward

The way litigation has been practiced for decades is cracking - and the lawyers who see it first will win. Recorded live at Legalweek 2026, host David Cowen sits down with Jeffrey Chivers, CEO of Syllo, to unpack why AI isn't just automating legal tasks - it's collapsing the traditional litigation workflow entirely. The path from discovery to trial-ready strategy is getting shorter. The question is: which legal professionals will adapt in time? What you'll learn: Why the litigation AI market has officially matured - and who's winning How Syllo was built by a litigator for litigators, not as a generic platform Why the old step-by-step workflow is dead - and what's replacing it What associates are really feeling right now, and what they need to hear Why 2025–2026 may be the most career-defining window in modern legal history

What happens when AI meets one of the most risk-sensitive professions in the world? In this episode, David Cowen sits down with KPMG partner Ed Gill to unpack how AI, operating models, and contract intelligence are reshaping the business of law. The real shift isn't just new tools - it's a new mindset where lawyers move from doing the work to orchestrating humans, workflows, and AI agents. Hosted by David Cowen Key Topics Covered Why people, process, and technology - in that order - determine whether legal AI actually delivers results The Ford assembly line analogy for law: how breaking legal work into workflows unlocks massive efficiency gains Why buying AI tools without redesigning the operating model almost always fails The rise of AI agents as "digital teammates" that extract clauses, analyze risk, and automate contract review How one global company is redesigning its legal function to cut 12,000 contracts down to 5,000 through standardization The hidden enterprise opportunity: poor contract management may cost companies up to 11% of revenue each year Why the lawyer of the future becomes the conductor of an AI orchestra rather than the person playing every instrument

Regulators finally caught up to how business actually happens: over text, WhatsApp, and mobile apps. In this year-end conversation, David Cowen sits down with Matt Rasmussen, Founder of ModeOne, to unpack why off-channel mobile data has become a $6B compliance problem and a massive opportunity for legal, IT, and ops professionals. Listeners will walk away with a clear view of where regulation is heading, where talent demand is exploding, and how to future-proof a legal career without chasing hype. Key Topics Covered Why email, Slack, and Teams are no longer enough to satisfy regulators and what replaces them The regulatory shift driving mobile collection at unprecedented scale (from 12 phones to 10,000+) The hidden "tax" of smartphone non-compliance, including billions in fines and stranded hardware How remote, scoped mobile collection reduces privacy risk while increasing defensibility Where talent demand is surging most: corporate legal, legal ops, and forensic hybrid roles How to use the "12% AI dividend" to pivot into high-growth forensic and compliance work A practical weekend playbook for upskilling: case law, OS changes, and encryption updates Special Shoutout:  Scott Milner – Recognized for bridging deep technical expertise with practical leadership in eDiscovery and regulatory strategy Greg Mazares – ModeOne board member and trusted mentor, shaping how technology is applied to real client problems Jerry Bui (Purpose) – Cited for his perspective on the growing importance of forensics in modern legal workflows Nathaniel Whittemore – Host of The AI Daily Brief, referenced for framing the MIT insight on task-level automation Joseph Pochron – Nardello, recommended as a future guest for his visibility into corporate investigations and compliance Anthony Cardine  – O'Melveny & Myers, highlighted for his leadership at the intersection of eDiscovery, paralegal teams, and operational change

Steno's COO, Prabhdeep Singh joins David Cowen to break down why 2025 was the year AI finally got real in legal and what that means for 2026 and beyond. They explore how Steno is turning "data exhaust" into strategic advantage, why outsiders are reshaping the business of law, and what talent will define the next era. This episode is a roadmap for anyone looking to move from now to next in a rapidly shifting industry. Key Topics Covered How AI shifted from "shiny object" to budget line item and how that changed client expectations overnight. Why the real competitive edge isn't the model you use, but the data and distribution you control. The outsider advantage: lessons Prabh brought from Uber, WeWork, and Clover Health into legal tech. Inside-out vs. outside-in innovation and why blending both is the only sustainable path. Why trust, not technology, still wins deals in a crowded legal tech landscape. The rise of the "core four": how internal evangelists drive firm-wide adoption and culture change. Predictions for 2026–2027: industry shakeouts, left-field entrants, and the next wave of legal transformation.

In a rare, candid roundtable, five of the most influential Chief Innovation Officers in Big Law join David Cowen to reveal how their roles and the entire legal industry have transformed in just the last 18 months. This episode pulls back the curtain on the strategic, operational, and cultural shifts that are redefining how modern law firms operate. From AI adoption to talent design to client co-creation, this conversation uncovers the real work happening inside elite firms and why the next decade of legal will look nothing like the last. If you want to understand where legal innovation is actually headed (beyond the hype), this is the episode. Featuring: Gina Lynch (Paul Weiss) David Wang (Cooley) Joe Green (Gunderson Dettmer) Annie Datesh (Wilson Sonsini) Matt Beekhuizen (Greenberg Traurig) KEY TOPICS COVERED How the CINO role moved from back-office function to firmwide strategic leadership Why GenAI forced a shift from point solutions to holistic, systems-level strategy The rise of client co-creation and why CINOs now spend more time with clients than ever What tech is showing real promise and what's still overhyped The biggest mistake clients make when implementing AI The new talent model: multidisciplinary teams, communication skills, and radical curiosity What future legal leaders need to understand about innovation careers

In this episode of Careers and the Business of Law, David Cowen explores a provocative idea: every billion dollars invested in AI and infrastructure generates an exponential surge in legal work. So what does that mean for the future of legal careers, legal operations, and the business of law? Joining David are Omar Haroun, Founder and CEO of Eudia, and Alison Zoellner, Group General Counsel at Dentsu Global. Together, they unpack how global AI investment is reshaping legal demand, talent models, and the very definition of what lawyers do. They address a critical misconception: while some focus on potential job loss, the real story may be the opposite. Massive AI and data infrastructure expansion is unlocking legal complexity across real estate, IP, regulatory structures, tax, contracting, and global compliance - creating far more legal demand than traditional models ever anticipated. Omar explains why pairing engineering talent with elite legal judgment is becoming the new competitive edge, while Alison brings the in-house perspective on responsible leadership, managing disruption, and preparing teams for the work AI is actually creating. This conversation goes beyond automation to ask a bigger question: if every wave of AI investment multiplies legal work, are we entering the largest legal growth cycle of our lifetime? Key Topics Covered Why AI infrastructure investment is driving legal demand The shift from time-based work to outcome-driven value Lawyers plus AI engineers as the core legal team Breaking down silos to build integrated decision systems Responsible leadership and preparing talent for change

November 21, 2025 ~ David Cowen, chief public spaces officer at the Downtown Detroit Partnership, joins Chris, Lloyd, and Jamie to preview tonight's Christmas tree lighting! Hosted by Simplecast, an AdsWizz company. See https://pcm.adswizz.com for information about our collection and use of personal data for advertising.

In this Careers and the Business of Law | Pre-TLTF Series conversation, David Cowen sits down with Tim Follett, Founder and CEO of StructureFlow, to explore how visual intelligence and AI agents are reshaping how legal and financial professionals work with complex data. From turning static charts into dynamic, interactive systems to teaching AI to see structures the way lawyers do, Tim shares a clear, forward-looking view of the next chapter in legal tech and what he's launching on the TLTF stage in Austin. Key Topics Covered: How visualization unlocks cognitive power in complex legal and corporate structures. Tim's AI-first workflow at StructureFlow, from meeting transcripts to intelligent summaries. Why personal knowledge management (PKM) and visual databases are the next frontier for professionals. The shift toward agentic and digital workforces and how StructureFlow is applying them today. Why 2025 is the year of AI generalists, and 2026 will belong to domain-specific innovators. How forward-deployed engineers and domain experts are changing the client experience. A sneak peek at StructureFlow's new brand and vision, launching live at the TLTF Summit.

In this Careers and the Business of Law | Pre-TLTF Series episode, David Cowen sits down with James Ding, CEO and Co-Founder of DraftWise and former Palantir engineering lead, to explore how data, accountability, and forward-deployed engineering are reshaping the business of law. From mobilizing firm knowledge to the philosophical lessons behind "Stillness is the Key," James shares a rare blend of technical insight and human wisdom ahead of the TLTF Summit in Austin. Key Topics Covered: How DraftWise turns legal data into actionable intelligence through digital twins of firm knowledge. The difference between a consultant and a forward-deployed engineer and why accountability is the real differentiator. Lessons from Palantir's customer-first model and how it inspired a new standard in legal AI. Why TLTF feels like a Michelin-star experience - a curated mix of funders, founders, and innovators. How cross-generational collaboration is driving innovation across law and tech. What James is reading and how "Stillness is the Key" informs his leadership philosophy. Why focus is more valuable than information in the age of AI abundance.

In this episode of Careers and the Business of Law, Pre TLTF conversation, David Cowen sits down with Dr. Hemma Lomax, Deputy General Counsel at DocuSign, to explore how intelligent agreement management is transforming legal operations and compliance. From turning static contracts into data-rich insights to empowering legal teams as strategic business partners, Hemma shares how technology, ethics, and leadership intersect in this new era of legal intelligence. Key Topics Covered: How DocuSign evolved from e-signatures to intelligent agreement management. The "agreement trap" and how legal teams can unlock trapped value in contracts. Why legal and compliance professionals should focus less on data entry and more on strategy. The rise of Legal Data Intelligence (LDI) and how it's reshaping the business of law. Insights from DocuSign's acquisition of Contract Nerds and what it means for the future of collaboration. Why being "in the arena" matters more than perfection, lessons from leadership and podcasting. The Davos of Legal Tech: what to expect from the TLTF Summit and the innovators shaping it.

In this Careers and the Business of Law | Pre-TLTF conversation, David Cowen sits down with Tom Dreyfus, CEO and Founder of Josef, to unpack what it really takes to build and scale a legal tech startup from the ground up. From the first Legal Tech Fund investment to today's thriving TLTF community, Tom shares unfiltered insights on grit, growth, and redefining success beyond the 9-9-6 grind. Key Topics Covered: The founder's journey: how Josef became the Legal Tech Fund's first portfolio company. Why relationships and listening matter more than capital in startup growth. The evolution from outsider to insider in the TLTF community and what that feels like. Why there are no shortcuts in building a meaningful business or reputation. The balance between grit and grace, navigating startup life and parenthood. How TLTF built a warm, human-centered community in an industry full of transactional events. A reflection on privilege, partnership, and progress in modern leadership.

In this episode of Careers and the Business of Law - Legal Data Intelligence seriese, David Cowen sits down with Odette Claridge (ProSearch), Tara Lawler (Morgan Lewis), and Virginia Ring (Kilpatrick Townsend) to unpack how Legal Data Intelligence (LDI) is transforming mergers, acquisitions, and divestitures. They share how data governance, AI, and collaboration are reshaping due diligence and deal execution and why frameworks like LDI's toolkit are now must-haves for modern legal teams. Key Topics Covered: How LDI's corporate working group built the first data-driven toolkit for M&A and divestitures. Why today's M&A landscape is defined by the 3 Vs of data, volume, variety, and velocity. Practical steps for maintaining data integrity and audit trails across multiple corporate entities. The new reality: collaboration between legal, IT, privacy, and compliance is non-negotiable. How crowdsourcing best practices across firms accelerates learning and innovation. What the Architect Program offers for professionals eager to shape the next wave of legal data frameworks. A look ahead: AI governance and ethical frameworks as the next frontier for legal data professionals.

In this episode of Careers and the Business of Law, David Cowen sits down with Nathan Reichardt, PwC's Lead Managed Services Director and AI Champion, for a conversation that bridges technology and humanity. They unpack why “observability” isn't just a technical concept, it's the foundation of trust in an age of autonomous agents. From building glass-box systems that make AI accountable to recognizing the invisible pressures on professionals, this discussion explores what it really takes to lead responsibly in the era of AI. Key Topics Covered: Agents aren't magic, you must observe them. Why oversight is essential as AI agents act and learn autonomously. From black box to glass box. Transparency, explainability, and compliance as non-negotiable design principles. Responsible AI in practice. What observability really means for governance, risk, and trust. The rise of new roles. Why “AI Observer” and “Observability Lead” may soon become critical titles inside legal and business ops. The human dimension. How leaders can apply observability to people spotting stress, isolation, and burnout before it's too late. From pilot to practice. PwC's approach to scaling agentic AI safely through iteration, measurement, and feedback.

October 7, 2025 ~ David Cowen, Chief Officer of Parks and Public Spaces Downtown Detroit Partnership joins Eric Larson in for Paul W Smith. Hosted by Simplecast, an AdsWizz company. See https://pcm.adswizz.com for information about our collection and use of personal data for advertising.

Big thanks to ThreatLocker for sponsoring my trip to Black Hat 2025. To start your free trial with ThreatLocker please use the following link: https://www.threatlocker.com/davidbombal In this interview from Black Hat 2025, David Bombal sits down with two cybersecurity legends: David Cowen (Digital Forensics Expert) and Evan Anderson (Red Team Operator and Tool Builder). They give an unfiltered look at the real world of hacking, forensics, and career-building in cybersecurity. What we'll cover: • How the SolarWinds hack was discovered with never-before-heard forensics insight • Real-world red teaming using HVAC exploits, USB pivots, and AWS chaos • The Oculus vs. Carmack lawsuit story from the expert who worked the case • How to start your career in cybersecurity, even without a degree • What the CCDC program is and why it leads to 3 job offers instantly • How AI is changing the game for hackers and defenders alike // David Cowen's SOCIALS // SANS Profile: https://www.sans.org/profiles/david-c... LinkedIn: / dcowen X: / dcowen // Evan Anderson SOCIALS // Offensive Context: https://blog.offensivecontext.com/aut... LinkedIn: / syndrowm GitHub: https://github.com/syndrowm // Website REFERENCE // https://www.nationalccdc.org/ https://www.sans.org/emea https://ctftime.org/ https://www.uscyberpatriot.org/ // YouTube Channel REFERENCE // 13Cubed: / @13cubed // David Cowen's Books REFERENCE // Computer Forensics: US: https://amzn.to/47yeH70 UK: https://amzn.to/460ErGs Hacking Exposed Computer Forensics: Secrets and Solutions US: https://amzn.to/4mYevCW UK: https://amzn.to/46q07NH Hacking Exposed Computer Forensics: Secrets and Solutions: US: https://amzn.to/4mT3T8k UK: https://amzn.to/4m8zaCS // David's SOCIAL // Discord: discord.com/invite/usKSyzb Twitter: www.twitter.com/davidbombal Instagram: www.instagram.com/davidbombal LinkedIn: www.linkedin.com/in/davidbombal Facebook: www.facebook.com/davidbombal.co TikTok: tiktok.com/@davidbombal YouTube: / @davidbombal Spotify: open.spotify.com/show/3f6k6gE... SoundCloud: / davidbombal Apple Podcast: podcasts.apple.com/us/podcast... // MY STUFF // https://www.amazon.com/shop/davidbombal // SPONSORS // Interested in sponsoring my videos? Reach out to my team here: sponsors@davidbombal.com // Menu // 0:00 - Coming up 0:49 - Intro 01:13 - Sponsored Section 01:29 - (AWS) Amazon Web Services 03:04 - David Cowen's Background 03:46 - Evan Anderson's Background 05:18 - Advice for young people To Get A Job In this Space 05:56 - The Solar Winds Hack? 10:43 - Finding a needle in a Haystack 11:08 - The Oculus Story 13:00 - Evan in Red Teaming 15:55 - Advice To Younger self 16:51 - Recommended Courses 19:42 - Importance of Networking 20:19 - Recommended Certifications 24:13 - Is AI Taking All The Jobs ? 24:57 - Connect With David & Evan online 25:12 - Conclusion & Outro Please note that links listed may be affiliate links and provide me with a small percentage/kickback should you use them to purchase any of the items listed or recommended. Thank you for supporting me and this channel! Disclaimer: This video is for educational purposes only.

What happens when AI gets faster than your legal team? In this episode, we're pulling back the curtain on the real disruption happening inside law firms, legal departments, and software giants. Microsoft's E.J. Bastien and Relativity's CTO Keith Carlson join David Cowen for a no-holds-barred conversation on AI's impact on legal strategy, workflows, careers and how everything is being redefined. If you're in legal, tech, ops, or just wondering what your job looks like in 24 months, this is the episode. Key Topics Covered: The AI Wake-Up Call: Why “change resistance” in legal is dead and what's replacing it The End of Legal Busywork: How AI is freeing up law firms for high-value thinking Billable Hour vs. Business Model: The quiet collapse of traditional legal pricing Speed to Insight: Why fast isn't fast enough anymore and how top teams are adapting Dark Data, Bright Future: New AI tools surfacing value where no one was looking Career Acceleration: Why critical thinkers, puzzle-solvers, and AI-curious pros are thriving The AI-Ready Org Chart: What the “firm of the future” looks like (hint: it's flatter and faster)

LET THE CITY KNOW: You can also watch this episode via YouTube. In this installment of J.T. the L.A. Storyteller Podcast, guest David Cowen and I discuss his being diagnosed with bipolar disorder as early as when he was 21 years old, Kabbalah and Zionism, Israel’s genocide through forced starvation in Gaza, as well asContinue reading FROM L.A. TO KHAN YUNIS: ALL EYES ON GAZA →

What separates a legal department that saves money from one that builds competitive advantage? Two powerhouse CLOs, Rishi Varma (Cargill) and Tim Fraser (Toshiba America) - sit down with David Cowen to unpack the shift from legal risk managers to business growth drivers. If you're a legal leader, strategist, or tech-savvy operator, this is essential listening. The future isn't coming. It's here. And these leaders are already in it. Key Topics Covered: The AI Dividend: What it is, how to measure it, and why it's your next performance metric Data as Infrastructure: Why CLOs are racing to eliminate the “search function” and build a legal “brain” OKRs That Matter: How top legal departments align KPIs to business growth, not compliance checklists Tech Stack in Action: Inside the tools (Copilot, GenAI) that are driving real productivity gains today Talent Evolution: What CLOs actually look for in 2025, critical thinking, adaptability, and strategic fluency Cross-Functional Power Moves: Why your next big win requires partnering with your CIO (or CEO) From Perfection to Performance: Why "excellence over perfection" is the new rule of law

What if one judge kills GenAI in court? Former U.S. Magistrate Judge Andrew Peck says it could set legal innovation back a decade. In this episode, David Cowen and co-host Nicole Giantonio go inside the mind of the “Godfather of eDiscovery” to unpack the real risks, courtroom landmines, and what every lawyer needs to know before using AI in a case. This isn't theory. It's already happening. What You'll Learn: Why one bad GenAI ruling could halt progress for 10 years How “hallucinated” case law is already damaging court credibility The question no one can agree on: Are AI prompts discoverable? What smart firms are doing right now to stay defensible Why your judge's tech IQ might matter more than your case facts The #1 safeguard Judge Peck says you must have in place today What DLA Piper is doing that most law firms still haven't figured out

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

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. 

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

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?

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.

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.

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

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.

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

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.”                                                           

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.