Notes to My Legal Self®

Welcome to Season 15, Episode 2 of Notes to My (Legal) Self , where host Olga V. Mack sits down with Elizabeth Colombo, Associate General Counsel at Vendavo. Together, they explore why great negotiation is about more than contracts. Beth shares practical lessons on empathy, business judgment, communication, and how in-house lawyers can become trusted business partners in an AI-assisted world. In t...

Welcome to Season 15, Episode 1 of Notes to My (Legal) Self. Olga Mack sits down with Alexandra Sepulveda, Associate General Counsel at Trust & Will, to explore one of the biggest questions facing the legal profession today: How do we raise lawyers who can think when AI does the thinking? Together, they examine why judgment, not just knowledge, will define the next generation of legal professi...

Welcome to Season 14, Episode 10 of Notes to My (Legal) Self®. In this thought-provoking conversation, host Olga Mack sits down with Dharshi Harindra, Assistant General Counsel, APAC at FTI Consulting, to explore one of the most important questions facing the legal profession today: When AI starts doing lawyers’ work, what labels still matter? Together, they examine the evolving role of lawyers in...

Welcome to Season 14, Episode 9 of Notes to My (Legal) Self. In this episode, host Olga Mack sits down with Cherryn-Paige Bissett, commercial attorney and Internal Commercial Counsel at LegalSifter, to explore how legal professionals can leverage AI without sacrificing human judgment. Together, they discuss the practical realities of contract automation, the role of playbooks, and why the most val...

Welcome to Season 14, Episode 8 of Notes to My (Legal) Self. In this episode, host Olga Mack sits down with Matthew Thomas to explore one of the most valuable, and often misunderstood, skills in legal practice: judgment. Together, they discuss how good judgment is developed through experience, mistakes, mentorship, and perspective. From navigating complex negotiations and managing risk to leading...

Welcome to Season 14, Episode 7 of Notes to My (Legal) Self. In this episode, host Olga Mack sits down with Marco Imperiale to explore a fundamental question: Do lawyers truly understand the people they serve? Together, they examine how legal design, curiosity, communication, and human-centered thinking are reshaping the future of legal practice. From client engagement to innovation, Marco challen...

Welcome to Season 14, Episode 6 of Notes to My (Legal) Self. In this episode, host Olga Mack sits down with Angela Madathil for a thoughtful conversation on compliance, AI, storytelling, and the future of legal leadership. Angela shares how her experience supporting technology initiatives inside the trucking industry shaped her approach to compliance, product counseling, and responsible innovation...

In this episode, host Olga Mack sits down with Geoffrey Brow for a fascinating conversation about building legal infrastructure for breakthrough technologies. Geoffrey shares his journey from international law and corporate practice in New York and London to becoming a technology transactions leader working with companies like Dell, Google, AT&T, Roku, and Virgin Hyperloop. Throughout the conv...

Are you relying on certainty… or building better judgment in uncertain times? In this episode of Notes to My (Legal) Self® , Olga Mack speaks with Carolyn Herzog, Chief Legal Officer at Elastic, a global search AI company, about leading through disruption, navigating AI, and redefining resilience in the legal function. As the pace of change accelerates, from AI to geopolitical shifts, legal teams...

Are you optimizing your outsourcing deals for price… or for long-term success? In this episode of Notes to My (Legal) Self® , Olga Mack speaks with Irina Beschieriu, an attorney specializing in complex outsourcing and global service delivery models, with deep expertise in cross-border technology transactions, vendor governance, and AI-driven services. As outsourcing evolves beyond cost-cutting int...

Are depositions now more important than trials in litigation strategy? In this episode of Notes to My (Legal) Self® , Olga Mack speaks with Dean Whalen, Chief Legal Officer at Readback, who brings over two decades of litigation and legal leadership experience at the intersection of law and technology. As trials become increasingly rare, modern litigation is shifting toward discovery, where deposit...

In this episode, host Olga Mack sits down with Jessica Nguyen and Nada Alnajafi for an honest and energizing conversation about what happens when in-house lawyers build beyond their day jobs, and how personal brands, communities, and bold decisions create real leverage. Nada Alnajafi is Senior Corporate Counsel and Lead Legal Ops at Franklin Templeton and the founder of Contract Nerds, a community...

In this episode of Notes to My (Legal) Self®, host Olga V. Mack speaks with Heath Morgan, in-house attorney and author of The Memory Project, about memory, identity, and the long-term ethical implications of AI adoption. Drawing from his experience in cybersecurity, compliance, and AI governance, as well as his speculative fiction work. Heath explores what happens when technology allows us to pres...

In this episode of Notes to My (Legal) Self®, host Olga V. Mack speaks with Rina Wang, former Assistant General Counsel at AI startup Prepared, about what it really means for lawyers to build a career inside venture-backed startups, especially during periods of uncertainty, hypergrowth, and rapid change. Drawing from her journey across litigation, multiple venture-backed startups, and a recent acq...

In this episode of Notes to My (Legal) Self®, host Olga V. Mack sits down with John Pavolotsky, technology transactions attorney, privacy and cyber expert, and co-head of the AI practice at Stoel Rives, to unpack the fast-changing world of AI contracting. With 25 years of experience across startups, Big Tech, and private practice, John brings a grounded, practical view of how lawyers can draft, ne...

In this episode of Notes to My (Legal) Self , host Olga V. Mack talks with Carl Davidson , a former immigration attorney turned product leader and now co-founder of Candle AI , about one of the biggest pain points in legal practice: email overload, and why he left law to fix it. Carl recounts his path from corporate and immigration law to Silicon Valley, where he saw firsthand how constant client...

In this full episode of Notes to My (Legal) Self , host Olga V. Mack sits down with Dorna Moini , CEO and founder of Gavel , to explore how automation, no-code tools, and AI are empowering lawyers to scale their practice, streamline workflows, and expand access to justice, without burning out or billing more hours. Dorna shares her journey from Big Law litigator at Sidley Austin to legal tech entr...

In this full episode of Notes to My (Legal) Self, Karl Seelbach, litigation attorney and founder of Skribe.ai, explores how technology and AI are reshaping courtroom practice, legal testimony, and the very fabric of the litigation process. Karl shares his journey from a traditional courtroom litigator defending Fortune 500 companies to building a software platform that makes capturing legal testim...

In this episode of Notes to My (Legal) Self®, Olga V. Mack sits down with Senne Mennes, former Big Law lawyer turned Co-Founder of ClauseBase, a company revolutionizing how legal professionals draft documents using automation and AI-powered tools. Together, they explore how Senne transitioned from traditional legal practice to entrepreneurship—and what every lawyer can learn from his journey. Here...

Season 13, Episode 3: Legal Tech Disruptors, New Minds Innovating for Good (ft. Kara Peterson) In this episode of Notes to My (Legal) Self®, host Olga V. Mack sits down with Kara Peterson , a marketing communications leader and co-founder of descrybe.ai, a legal tech startup democratizing access to legal information through AI. Kara’s story is as inspiring as it is unexpected. Coming from a backgr...

Season 13, Episode 2: The Gig Economy for Lawyers is Coming (ft. Otto Hanson) In this episode of Notes to My (Legal) Self, host Olga V. Mack sits down with Otto Hanson, Co-Founder and CEO of TermScout and Screens, for a forward-looking conversation about innovation, productization, and trust in legal technology. Otto shares how TermScout became the first platform to certify fairness in B2B contrac...

In this full episode of Notes to My (Legal) Self, Olga V. Mack sits down with Basha Rubin, CEO and Co-Founder of Priori to explore how legal marketplaces are transforming the way in-house teams find, hire, and manage outside counsel. Basha shares her journey from Yale Law School during the 2008 recession to co-founding Priori in 2013, and how the company evolved from serving individuals and small...

In this episode of Notes to My (Legal) Self , Olga Mack sits down with Adriana Dulic, Chief Compliance Officer at a leading fintech company, to explore the powerful intersection of legal compliance, leadership, and service. Adriana shares her journey from private practice to a long-term in-house and compliance career, shaped by the dynamic world of financial technologies and regulatory change. But...

The boundaries of a legal career are wider than you think. In this episode, Avril Sisk—independent corporate director and former judge—joins Olga Mack to explore how legal professionals can lead beyond traditional practice and reshape industries, communities, and boardrooms. With a career spanning public policy, nonprofit leadership, the judiciary, and corporate governance, Avril shares her inspir...

In the season finale of Notes to My (Legal) Self, Olga Mack is joined by Tara Emory—former big law antitrust attorney, general counsel, and legal tech consultant—for a candid conversation on how legal teams can overcome cultural and organizational resistance to GenAI. With two decades of experience at the intersection of law and technology, Tara shares her evolution from litigator to legal innovat...