The Abstract

What’s on the bookshelf of today’s top legal leaders? In this special bonus episode, host Tyler Finn asks general counsels, founders, and legal innovators one simple question: What book would you recommend to our listeners?From legal thrillers to leadership classics, personal growth memoirs to spiritual texts — the answers are as wide-ranging as the roles these leaders play. Hear how books like Give and Take, The Culture Code, Ikigai, The Hard Thing About Hard Things, and 100 Saturdays have helped shape how these professionals think, lead, and live.Whether you're looking for your next business read or something more soul-stirring, this episode is your perfect reading list.Read detailed summary: https://www.spotdraft.com/podcast/episode-109   Topics Introduction: 00:00Rob Chesnut, Former GC and CEO at Airbnb, on writing a book that started as a dinner-table idea: 00:33Dana Rao, Former GC & CTO, Adobe, on falling for fiction through Here One Moment by Liane Moriarty: 05:52Shashank Bijapur, Co-Founder & CEO, SpotDraft, on how Zero to One and The Hard Thing About Hard Things guided his transition from lawyer to founder: Akshay Verma, COO at SpotDraft, on the leadership lessons from Getting Naked: 07:07Tim Hirsch, GC of Mars Science & Diagnostics, on the untold Holocaust history in 100 Saturdays: 08:48Manu Kanwar, Founder and CEO, LexSolutions, on trauma, ADHD, and human flourishing: 11:17Alex Herrity, Director of Global Legal Solutions, Adidas, on contract design and building a second brain: 14:52Keita de Souza, GC at Ryse, on Likable Badass and redefining influence: 17:00David Cowen, President at The Cowen Group, on how books shape leadership and connection: 19:33Joon Park, Chief Legal Officer at Extend Enterprises, Inc., on the spiritual depth of the Tao Te Ching and his wife's Pulitzer-winning biography: 21:14Tyler Finn, Head of Community & Growth at SpotDraft, on books that shaped his values, legal curiosity, and political awareness: 23:01    Connect with us: Tyler Finn - https://www.linkedin.com/in/tylerhfinnSpotDraft - https://www.linkedin.com/company/spotdraftSpotDraft is a leading contract lifecycle management platform that solves your end-to-end contract management issues. Visit https://www.spotdraft.com to learn more.

What happens when a former law firm CMO and Uber’s head of legal ops pulls back the curtain on the business of law? In this episode, Tyler Finn sits down with Ken Callander, Managing Principal at Value Strategies, to explore the evolution of law firm pricing, the rise of AI, and how in-house teams can save millions by shifting to value-based fee arrangements. From the politics of partnerships to actionable strategies for better outside counsel management, Ken brings unmatched candor and clarity on how legal teams must adapt in a rapidly evolving landscape.   Read detailed summary: https://www.spotdraft.com/podcast/episode-108   Topics Introduction—0:00How Law Firm Business Models Drive Political Risk-Taking and Brand Fallout – 01:49Inside the Law Firm Model: Power Partners, Payout Structures, and Why Change is So Hard—09:02Challenges with hourly billing and how law firm economics are misaligned with client value—16:32Why Ken left the law firm world for legal ops at Uber—26:34Moving to value-based pricing and how it impacted Uber’s legal spend—30:10Why predictability in pricing is often more important than savings—34:21How AI is disrupting law firm pricing, staffing, and the associate career path—37:33How In-House Teams Can Improve Law Firm Relationships, Reduce Spend, and Drive Change—49:14Rapid-fire questions—56:25Connect with us:Ken Callander - https://www.linkedin.com/in/kencallander/Tyler Finn - https://www.linkedin.com/in/tylerhfinnSpotDraft - https://www.linkedin.com/company/spotdraftSpotDraft is a leading contract lifecycle management platform that solves your end-to-end contract management issues. Visit https://www.spotdraft.com to learn more.

In this episode of The Abstract, host Tyler Finn sits down with Andrew Epstein, General Counsel of Demandbase, for a candid conversation on building a legal career rooted in curiosity, intentionality, and creative risk-taking. From starting his career in the GC’s office of the Washington Nationals to handling high-stakes spinouts at LiveRamp, Andrew shares how he made bold choices, built trust across functions, and scaled legal teams strategically. He dives deep into building legal ops, leveraging AI thoughtfully, and what it really takes to thrive as a first-time GC. A must-listen for in-house leaders, aspiring GCs, and legal professionals navigating a rapidly evolving legal landscape.Read detailed summary: https://www.spotdraft.com/podcast/episode-107TopicsIntroduction – 00:00Andrew’s intentional path to law school and first job at a GC’s office – 02:28Working for the Washington Nationals and using that experience to stand out – 04:38Choosing O’Melveny for its cross-office structure and California links – 08:10From Capital Markets to Privacy: Why Andrew Left Big Law for In-House at LiveRamp – 09:49Managing complex transactions: M&A, spinout from Axiom, NYSE listing – 17:18Privacy, Adtech, and Proving Your Value in a Changing Legal Team – 22:04Getting hired as GC at Demandbase through cross-functional trust – 27:33Scaling the legal team intentionally for IPO readiness – 29:41Growing as a first-time GC through peer mentorship – 32:43Building a lean, flexible team that integrates AI and legal ops – 35:35Encouraging AI experimentation over shiny tools – 40:08Rapid-fire Question – 46:04Connect with us:Andrew Epstein - https://www.linkedin.com/in/andrew-epstein-3b22a471/Tyler Finn - https://www.linkedin.com/in/tylerhfinnSpotDraft - https://www.linkedin.com/company/spotdraftSpotDraft is a leading contract lifecycle management platform that solves your end-to-end contract management issues. Visit https://www.spotdraft.com to learn more.

What does it take to scale a legal team in high-growth environments? In this special bonus episode of The Abstract, we feature insights from five legal leaders who have each helped their organisations scale — and survived the chaos that comes with it.From building global teams at Carta to laying the legal foundation at early-stage startups, our guests reflect on the personal and professional lessons learned along the way. You’ll hear how legal ops, AI adoption, prioritisation frameworks, and even IKEA furniture assembly play a role in building agile, resilient legal teams. Whether you're the first lawyer in the door or leading a 50-person department, this episode is packed with takeaways for legal professionals navigating scale.Read detailed summary: https://www.spotdraft.com/podcast/episode-106   TopicsIntroduction - 0:00April Lindauer, GC at Carta, on scaling legal from 200 to 2000 employees post-Series C – 0:35Adam Becker, Head of Legal Ops at Cockroach Labs, on building connective legal infrastructure and enabling smarter AI adoption – 2:42David Cowen, Founder of The Cowen Group, on legal ops maturity and leading in the age of AI agents – 4:54Tommie Tavares-Ferreira, Chief Strategy Officer, Lawtrades, on aligning legal priorities with business impact and enabling cross-functional trust – 8:52Jordan Hatcher, Co-Founder & CLO/COO, The Grid, on scaling legal internationally and staying grounded through hypergrowth – 14:11Connect with us:Tyler Finn - https://www.linkedin.com/in/tylerhfinn SpotDraft - https://www.linkedin.com/company/spotdraftSpotDraft is a leading contract lifecycle management platform that solves your end-to-end contract management issues. Visit https://www.spotdraft.com to learn more.

What if the legal system punishes the victim instead of the attacker? That question drives Andy Lunsford, founder and CEO of BreachRx, to rethink how companies prepare for and respond to data breaches.In this episode, Andy joins host Tyler Finn to share his journey from litigation consultant to legal tech entrepreneur—and why he believes incident response should be treated like any other core business process. Separating privileges from factual records to rethinking executive liability, Andy offers practical insights for legal counsels navigating a regulatory maze, rising risk, and increasing accountability.Read detailed summary: https://www.spotdraft.com/podcast/episode-105   Topics Introduction – 00:00Andy’s path into privacy law: From philosophy to shaping early FTC breach cases—02:07The shift from rare black swan breaches to everyday business risk—6:19How GDPR’s 72-hour rule changed incident response expectations – 08:54Founding Beacon Group: bridging litigation, incident response, and expert testimony—13:53The law punishes victims: why breach response is legally broken—16:53Defending the defenders: Mental toll and leadership under breach pressure—21:00Personal Risk in Cybersecurity: Why CISOs and Legal Leaders Need Protection Too – 22:48How GCs Can Prepare for Breaches: Building Systems, Not Just Plans—27:28Rising executive accountability: how GCs can protect their teams and companies—32:23From legal consultant to tech CEO: building BreachRx as a category-defining platform—34:49The challenge of early-market education and building industry standards—40:52Rapid-fire Questions—42:35  Connect with us: Andy Lunsford - https://www.linkedin.com/in/andersonlunsford/ Tyler Finn - https://www.linkedin.com/in/tylerhfinn SpotDraft - https://www.linkedin.com/company/spotdraft   SpotDraft is a leading contract lifecycle management platform that solves your end-to-end contract management issues. Visit https://www.spotdraft.com to learn more.

In this episode of The Abstract, host Tyler Finn is joined by Joon Park, Chief Legal Officer at Extend Enterprises, Inc., for a candid conversation about building a legal career defined by integrity, adaptability, and curiosity.   From navigating the collapse of Refco early in his career to leading legal at high-growth fintech companies, Joon shares how high-pressure moments shaped his risk mindset and leadership style. He unpacks why startups need legal guidance from day one, how to embed compliance without slowing down, and why modern legal counsel must be both partner and protector. Along the way, Joon reflects on finding purpose, embracing uncertainty, and staying curious through every chapter.   Read detailed summary: https://www.spotdraft.com/podcast/episode-104   Topics Introduction - 00:00 Early career influences: philosophy, parenting, and curiosity - 01:54 Holistic thinking and law as systems navigation – 05:00 Transitioning from Big Law to in-house for financial security – 07:01 Refco collapse: a crash course in legal ethics and resilience – 10:35 Risk mindset: documenting decisions and staying aligned – 14:05 Generalist vs. specialist: finding fit during the Citigroup bailout – 17:02 Moving to startups: autonomy, prioritisation, and risk ownership – 21:59 Legal as an enabler, not a blocker, in startup environments – 24:35 Building scalable compliance without killing speed – 26:17 Legal’s role in shaping company culture and accountability – 28:21 Following curiosity to stay motivated and engaged – 30:19 Rapid-fire Questions – 32:21   Connect with us: Joon Park - https://www.linkedin.com/in/joon-park-147a9a92/ Tyler Finn - https://www.linkedin.com/in/tylerhfinn SpotDraft - https://www.linkedin.com/company/spotdraft   SpotDraft is a leading contract lifecycle management platform that solves your end-to-end contract management issues. Visit https://www.spotdraft.com to learn more.

In this special episode of The Abstract, host Tyler Finn speaks with Tommie Tavares-Ferreira, newly appointed Chief Strategy Officer at Lawtrades and longtime legal ops leader, community builder, and podcast host.  Tommie walks us through her unconventional path from the music industry to Peloton, Rakuten, Cedar, and now the executive team at Lawtrades. She shares lessons on scaling companies, embracing curiosity, balancing parenting with leadership, and how legal ops leaders can (and should) step into strategy roles. It’s a personal, powerful conversation about evolving careers, future tech, and the next phase of legal work.Read detailed summary: https://www.spotdraft.com/podcast/episode-103 Topics: Introduction: 0:00Tommie’s early career in music, HBO, and the spirit of DIY creativity: 2:26Legal ops as a career by necessity, not design: 5:03Legal ops as a creative discipline and never-ending work: 6:53Helping businesses scale through legal ops alignment and prioritization: 8:39Love of technology, fears of automation, and the case for balance: 13:46Bringing legal teams into the AI journey and overcoming resistance: 19:24Why Tommie joined Lawtrades and what she hopes to build: 24:55Legal ops as strategy and expanding the role into go-to-market leadership: 33:15The glass ceiling in legal ops and the need for executive pathing: 36:52Rapid-fire questions: 41:17Connect with us: Tommie Tavares-Ferreira - https://www.linkedin.com/in/tommie/ Tyler Finn - https://www.linkedin.com/in/tylerhfinn SpotDraft - https://www.linkedin.com/company/spotdraft  SpotDraft is a leading contract lifecycle management platform that solves your end-to-end contract management issues.   Visit https://www.spotdraft.com to learn more.

In this special live-recorded episode of The Abstract from CLOC in Las Vegas, host Tyler Finn sits down with David Cowen, founder of The Cowen Group and creator of the SOLID Summit Series.David shares his journey from staffing to shaping the legal ops ecosystem, the moment he foresaw the rise of e-discovery, and why community is the most powerful response to chaos. He discusses the evolution of legal operations, the future of AI and agentic teams, and why trusting your talent matters more than ever. From frameworks on scaling legal to using ChatGPT as an executive coach, this episode offers a playbook for building a career and community in a rapidly changing industry.Read detailed summary: https://www.spotdraft.com/podcast/episode-102  Topics:Intro: 00:00David's career journey: From staffing to community building: 2:22The moment he discovered e-discovery's potential: 5:10How TED Talks inspired the SOLID Summit format: 6:49Chaos as the ideal condition for community building: 8:43Overbuilding in legal tech: problem or opportunity?: 10:52Spotting innovation through curiosity, not prediction: 13:02Legal Ops turns 10: What’s next for the profession?: 17:33Climbing the legal career “jungle gym,” not a ladder: 21:03How to manage anxiety and disruption in an AI-driven future: 25:53On coaching, preparation, and using ChatGPT as a partner: 28:25Legal Ops’ evolving role in helping businesses scale: 32:49The future of legal tech: use cases and AI agents: 37:12The GC as catalyst: Top-down transformation is here: 39:46Creators, Builders, Consumers: Who shapes the industry?: 42:54What excites David most about the next 10 years: 45:35Rapid-fire Questions: 47:25 Connect with us: David Cowen – https://www.linkedin.com/in/davidcowen/ Tyler Finn - https://www.linkedin.com/in/tylerhfinn SpotDraft - https://www.linkedin.com/company/spotdraft  SpotDraft is a leading contract lifecycle management platform that solves your end-to-end contract management issues.   Visit https://www.spotdraft.com to learn more.

What does it mean to lead legal operations when there’s no clear blueprint?In this episode of The Abstract, host Tyler Finn sits down with Adam Becker, Director of Legal Operations at Cockroach Labs and board member at CLOC, for a candid conversation about evolving careers, scaling legal departments, and the growing scope of legal ops. From breaking the “lawyer mold” to embracing AI-native strategies, Adam shares personal lessons on confidence, curiosity, leadership, and why legal ops is entering a new season of strategic impact.The discussion also explores how CLOC’s community and resources help elevate the field, and why every legal ops professional should see themselves as a partner to the GC — not just a process owner.Read detailed summary:  https://www.spotdraft.com/podcast/episode-101  Topics Introduction and career arc overview: 0:00 Early clues that pointed to process thinking: 1:14Breaking out of the lawyer mold and recognizing transferable skills: 2:09Confidence, curiosity, and pivoting into legal ops: 5:51Driving impact at MetLife and Endeavor: 8:33  Why legal ops requires conviction, not just thick skin: 11:09  The people-process-tech triangle — and why “people” matters more: 14:13  Culture and collaboration at Cockroach Labs: 16:36Balancing scale with flexibility in a fast-growing company: 18:53How legal ops has evolved through CLOC’s growth: 21:14Is legal ops at a crossroads? And what’s CLOC’s role in the future?:  26:22Rapid Fire: 32:59Connect with us: Adam Becker - https://www.linkedin.com/in/adam-becker-896a7a3/ Tyler Finn - https://www.linkedin.com/in/tylerhfinn SpotDraft - https://www.linkedin.com/company/spotdraft  SpotDraft is a leading contract lifecycle management platform that solves your end-to-end contract management issues.Visit https://www.spotdraft.com to learn more.

In the 100th episode of The Abstract, the mic flips as SpotDraft’s Chief of Staff, Nakta Alaghebandan, interviews our podcast’s usual host and creator, Tyler Finn.  From his start in public policy to shaping one of the most influential legal communities at SpotDraft, Tyler shares the pivotal career moments, risky leaps, and trust-building lessons that defined his path. He reflects on navigating early career detours, becoming a privacy leader despite skepticism, and building trust from scratch with executive stakeholders and customers.  The conversation dives deep into community-building philosophy, the value of calculated risk, and how Tyler sees “increasing your surface area” as the most underutilized career growth strategy. You'll also hear how the podcast came to life, what he’s learned after 100 episodes, and his advice for creating lasting impact — with humility, humour, and heart.  Read detailed summary:  https://www.spotdraft.com/podcast/episode-100  Topics Introduction: 0:00Tyler’s early pivot from public policy to legal tech: 3:15Choosing privacy despite warnings against it: 5:40Building trust after entering a low-trust role: 8:33Becoming the go-to for high-anxiety customer: 12:04Why cross-functional thinking matters in legal leadership: 15:52Sitting in the grey: layoffs, uncertainty, and consulting: 19:03Taking calculated risks and trusting your gut: 22:51From outsider to community leader at TechGC: 25:20What real community building looks like: 29:28  How to design a community where people actually open up: 30:55Building trust and reputation intentionally: 31:25How SpotDraft went from a consulting client to employer: 36:26Community as a future-facing marketing strategy: 40:18How Tyler now evaluates executive teams and companies: 43:22Why the CEO and executive team matter more than you think: 46:33What great executive teams do to support internal community: 47:42Why Tyler launched The Abstract and his goals for it: 50:12Personal lessons from 100 episodes: 56:04“Increasing your surface area” and embracing uncertainty: 1:01:56Favourite part of the day: 1:05:12Professional pet peeve: 1:06:11Book recommendations: 1:07:09Advice to younger self: 1:11:21   Connect with us: Tyler Finn - https://www.linkedin.com/in/tylerhfinn Nakta Alaghebandan - https://www.linkedin.com/in/nakta/ SpotDraft - https://www.linkedin.com/company/spotdraft  SpotDraft is a leading contract lifecycle management platform that solves your end-to-end contract management issues.   Visit https://www.spotdraft.com to learn more.