Notes to My Legal Self®

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 acquisition by Axon, Reena offers a candid perspective on what lawyers should expect when they step into startup life.Together, they explore:• Why uncertainty isn’t a flaw of startups; it’s a defining feature• How one year in a startup can feel like 10 years in a Fortune 500 company• What it means to make career decisions with limited information• How lawyers can shift from risk-avoidance to value creation in fast-moving environments• Why startups force accelerated learning, leadership, and personal growthIf you’re a lawyer considering a move into a startup or questioning whether speed, ambiguity, and change are worth the tradeoff, this conversation offers an honest look at the realities behind the hype. Explore more episodes, insights, and reflections at:🌐 www.notestomylegalself.com#NotesToMyLegalSelf #StartupLife #InHouseLegal #CareerGrowth #LegalLeadership #AIStartups

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, negotiate, and manage AI-related agreements when the regulatory landscape is evolving by the month.Together, they explore:• How to draft AI contracts amid shifting state and global regulations• What counts as “high-risk” use cases under laws like the EU AI Act and Colorado AI Act• How AI is changing traditional risk allocation, compliance, and licensing terms• Why lawyers must experiment with AI tools now to stay future-ready• The unique role in-house counsel play in shaping responsible AI adoptionIf you want a clear, candid look at the current and near-future state of AI contracting, and what legal teams should be doing today to prepare, this episode delivers essential insights from one of the field’s most experienced practitioners.Explore more episodes, blogs, and insights at our official site:🌐 www.notestomylegalself.com#AIContracting #LegalTech #LegalInnovation #FutureOfLaw #TechTransactions #AIRegulation

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 messages, fragmented data, and inbox chaos slow lawyers down. He realized the real bottleneck wasn’t the law, it was the inbox.Now building Candle AI, Carl is focused on reducing administrative drag, centralizing client context, and helping legal professionals reclaim their time by bringing structured data directly into email.Together, Olga and Carl explore what happens when a lawyer becomes a builder, and how fixing “small” workflow problems can create outsized impact across the legal industry.In this conversation, they explore:• Carl’s transition from practicing attorney to product manager at Intuit• How a lack of structured data creates chaos in legal workflows• Why email remains the #1 source of friction, stress, and lost time for lawyers• The “magic moment” principle in product design, and why it matters for adoption• How Candle AI brings case context directly into Gmail/Outlook to eliminate tab-switching• Why client communication still defaults to email despite modern tools• The rise of founder-builders in legal tech and the role AI plays in enabling them• Why small firms and solo practices must not be left behind in the AI revolutionKey Learning Outcomes:• Understand why email overload is a systems problem—not a personal efficiency failure• See how integrated AI can reduce context switching and reclaim billable time• Learn how to follow user pain to build products lawyers actually adopt• Explore how structured data unlocks powerful automation across the legal stack• Gain insight into the future of legal practice—and why lawyers who build will shape itIf you’ve ever felt buried under email, frustrated by scattered information, or curious about how AI can make legal work lighter, this episode will show you how one former attorney turned that frustration into a mission, and a company.🌐 Explore more episodes, blogs, and insights at:http://www.notestomylegalself.com#LegalInnovation #ProductManagement #LegalEmail #FutureOfLaw #NotesToMyLegalSelf

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 entrepreneur. Her pro bono work with domestic violence survivors inspired her to create an online tool that evolved into Gavel, a leading legal automation suite that helps lawyers build repeatable, rules-based systems for client intake, document drafting, and negotiation.Together, they unpack what it means to build, not bill, and how forward-thinking legal professionals can use technology to serve more clients with less effort.In this conversation, they explore:• What it means to productize your legal services and turn expertise into scalable offerings• How automation and AI can increase revenue without increasing billable hours• The difference between rules-based automation and generative AI, and when to use each• How Gavel helps lawyers build “TurboTax for law” solutions without writing a line of code• Real-world examples of scalable legal services that expand access to justice• Why legal education is shifting to teach lawyers how to build systems, not just spot issuesKey Learning Outcomes:• Learn how to scale your legal practice through automation and no-code tools• Understand how to combine rules-based logic and AI to improve speed and quality• Discover how automation frees up time for strategy, empathy, and client relationships• Explore practical ways to package your expertise into repeatable, revenue-generating systems• Gain insight into the future of legal practice, one built by lawyers who buildIf you’ve ever wondered how lawyers can scale with automation and move beyond the billable hour, this episode will show you how to start building smarter, not harder.🌐 Explore more episodes, blogs, and insights at:⁠ http://www.notestomylegalself.com#LegalTech #Automation #LegalAutomation #AccessToJustice #LegalInnovation

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 testimony faster, smarter, and more accessible. He unpacks the challenges of bridging law and technology, the ethics of AI in litigation, and what it takes to go from practicing lawyer to legal tech founder.Karl explores:• Why the traditional deposition process is costly, outdated, and ready for disruption• How Skribe.ai leverages software and AI to modernize testimony capture• The nationwide shortage of stenographers, and what “non-stenographic depositions” mean for the future• How remote technology can improve efficiency, access to justice, and judicial transparency• The ethical and practical implications of generative AI in law• Lessons from Karl’s entrepreneurial journey, from overbuilding MVPs to finding product-market fitKey Learning Outcomes:• Understand how AI is transforming depositions, hearings, and transcript creation• Learn how to navigate resistance to innovation in traditional legal practices•Gain insights into balancing ethics, technology, and client stewardship• Explore how GenAI can improve speed, accuracy, and access to justice• Discover what it takes to transition from litigator to legal tech innovatorIf you’re a litigator, in-house counsel, or legal tech enthusiast curious about how generative AI and software are transforming the legal landscape, Karl’s story offers a powerful look into the next chapter of modern law.🌐 Explore more episodes, blogs, and insights at:http://www.notestomylegalself.com#LegalTech #Litigation #AIinLaw #LegalInnovation #SkribeAI #NotesToMyLegalSelf

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’s what you’ll explore: • How Senne went from drafting contracts at DLA Piper Brussels to co-founding a legal tech company • The skills that truly transfer from law to entrepreneurship (and the ones you’ll have to learn fast) • Why redefining your relationship with risk is crucial for innovation and growth • Emerging trends shaping the future of legal careers, from Gen AI to new hybrid roles like legal engineers.If you’ve ever wondered what life beyond the traditional legal path could look like, this conversation will inspire you to chart your own route.🌐 Explore more episodes, blogs, and insights at:http://www.notestomylegalself.com#LegalInnovation #Entrepreneurship #InHouseCounsel #CareerPivot

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 background in public health and social justice, she never imagined she’d one day help build a legal AI company, let alone one that has summarized millions of judicial opinions across the U.S. for free.Together, Olga and Kara explore: • How AI can bridge the justice gap by making law more understandable and accessible • Why passion for justice isn’t limited to lawyers • The power of cross-disciplinary collaboration (and yes, the advantages of “marrying an engineer”) • What legal tech can learn from public health about tackling systemic inequitiesIf you’ve ever wondered how innovation, empathy, and a touch of humor can reshape access to justice, this conversation will leave you both informed and inspired.Explore more episodes, blogs, and insights at our official site: 🌐 www.notestomylegalself.com#LegalPodcast #InHouseCounsel #LegalTech #LegalInnovation #FutureOfLaw #AIinLaw #AccessToJustice #Leadership #LegalCareer

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 contracts, how Screens enables lawyers to build and share AI-powered contract playbooks, and why the next evolution of legal work will combine human expertise with technology, not replace it.Together, Olga and Otto explore:• How AI is unlocking new business models in law• What “productized legal services” mean for practitioners and clients• Why a trust gap still exists between lawyers and AI• How certification and transparency can reduce sales friction• The steps every lawyer can take to start experimenting with AI safely and effectively. If you’re curious about the intersection of AI, contracts, and the future of legal work, this episode will inspire you to think like a builder and have fun doing it.S U B S C R I B E!Thank you for watching!Like, Comment, Subscribe and hit the bell so you never miss an episode!Subscribe to our channel: @NotesToMyLegalSelf#GigEconomy #InHouseCounsel #ScreensAI #OlgaVMack #TermScout

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 businesses to partnering with Fortune 10 enterprises. Together, Olga and Basha dive into the rise of legal marketplaces, the role of data and AI in decision-making, and why alternative providers are reshaping the future of legal services.Together, Basha and Olga explore:• Why the traditional big law model underserves many clients• How in-house teams can categorize legal work by risk and complexity• Practical benefits of marketplaces for efficiency, cost savings, and expertise• The growing importance of data-driven, defensible legal decisions• How AI and technology are shaping the future of outside counsel managementKey Learning Outcomes:• Understand how legal marketplaces provide alternatives to big law firms• Learn strategies for smarter allocation of legal work across risk levels• Discover how data and scorecarding can improve outside counsel selection• Gain insight into the impact of AI on in-house counsel decision-making• Explore the future of legal services through Priori’s marketplace model. If you’re an in-house lawyer, legal ops professional, or legal leader seeking innovative ways to manage outside counsel, Basha’s insights offer a roadmap for embracing efficiency, transparency, and strategic value.

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 beyond her corporate role, Adriana offers a compelling case for why lawyers should make pro bono and community engagement a core part of their professional lives.In this conversation, you'll learn:What a day in the life of a CCO in fintech really looks likeHow compliance careers evolve with tech innovation and global oversightWhy pro bono work builds leadership skills and business acumenHow community service can ground legal careers in purpose and perspectiveWhat lawyers need to thrive in highly regulated, fast-paced industriesWhether you're charting a path in compliance, looking to make a meaningful career pivot, or seeking ways to serve beyond billable hours, this episode offers practical strategies and heartfelt insights on leading with integrity and impact.

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 inspiring journey and offers strategies for applying legal expertise across diverse sectors. If you've ever wondered how to take your legal career to new heights, this episode is for you.In this conversation, you'll learn:Why interdisciplinary skills are key to modern legal careersHow to transition into executive and non-legal leadership rolesThe value of community engagement in long-term professional successHow to pivot your career with resilience and purposeWhy viewing yourself as a client can transform personal developmentWhether you’re a lawyer exploring new horizons, a business leader looking to integrate legal insight, or someone passionate about community impact, Avril’s story will inspire you to reimagine the possibilities of a legal career.

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 innovator. Drawing on her in-house and consulting work, she breaks down what it really takes to bring GenAI into legal workflows in a way that sticks.In this conversation, you'll learn:Why legal tech adoption is as much about culture as it is about codeHow in-house teams evaluate legal tools through a cost–value lensReal-world use cases for GenAI—from drafting contracts to redline comparisonsHow to align GenAI initiatives with company culture and strategic goalsWhy GenAI should enhance human clarity, not replace legal judgmentWhether you're a GC evaluating tools, a legal ops leader planning implementation, or a skeptic wondering where GenAI fits in, this episode offers practical insights to guide your next steps.

The future of in-house leadership is bold, efficient, and business-driven. In this episode, Vinaya Ganesan, General Counsel for Europe at Firstsource Solutions, joins Olga Mack to share how GCs can do more with less—without compromising impact, innovation, or team morale.Drawing on her experience leading legal strategy for billion-dollar deals in tech and global outsourcing, Vinaya redefines what it means to be a modern, business-minded GC. From operationalizing legal strategy to empowering legal teams at every level, she shares actionable insights to elevate legal’s role across the enterprise.In this conversation, you'll learn:How to turn “more for less” into a legal leadership strategyHow to uncover hidden business pain points—and solve them proactivelyWhy empowering legal team members, including paralegals, fuels innovationWhat it takes to build trust and redefine the GC role as a business partnerScalable strategies to embed legal in operations and drive business outcomesWhether you’re a solo counsel, part of a lean legal team, or leading legal at the enterprise level, this episode is packed with insights on building agile, purpose-driven legal functions.

The path to a fulfilling legal career doesn’t have to be paved with burnout. In this episode, longtime trial lawyer turned coach Gary Miles joins Olga Mack to discuss how lawyers can transform stress into success and frustration into freedom.With over 45 years of legal experience, Gary shares practical tools and mindset shifts to help legal professionals manage imposter syndrome, avoid burnout, and build purpose-driven careers. Whether you're a new in-house counsel or a seasoned legal leader, this episode offers strategies to reclaim time, confidence, and clarity.In this conversation, you'll learn:How imposter syndrome manifests for in-house lawyers—and how to overcome itWhich key performance indicators (KPIs) lawyers should be trackingHow to structure your day for productivity and reduce burnoutThe value of unstructured time—and how to protect itHow to lead through service, not just conflictWhether you’re navigating your first legal role or rethinking your career after decades in practice, Gary’s insights are a powerful reminder that stress doesn’t have to define success in law.

The path to truly inclusive legal teams starts with one powerful trait: curiosity. In this episode, Niti Nadarajah—a former in-house lawyer turned leadership coach and DEI advocate—joins Olga Mack and co-host Memme Onwudiwe to unpack what it takes to build equity and belonging in the legal profession.With honesty and nuance, Niti challenges traditional hiring practices, exposes the hidden biases professionals of color face, and shares practical ways leaders can foster inclusion by asking better questions and listening more deeply.In this conversation, you'll learn:Why traditional “big law” pipelines fall short in building diverse teamsHow listening—really listening—can uncover blind spots and biasesHow healthy conflict can be a catalyst for innovation and better legal outcomesHow visual and verbal cues reveal hidden assumptions about socioeconomic statusStrategies for widening hiring funnels and redefining what it means to be “qualified”Whether you're building a legal team, mentoring future leaders, or navigating your career from an underrepresented background, this episode offers actionable insight for those serious about equity in law.

In this episode of Notes to My (Legal) Self, Olga Mack sits down with Shanti Ariker , a trailblazing Chief Legal Officer and tech veteran, to explore what it means to be the first lawyer at a fast-moving public company. In “First In-House,” Shanti reflects on her journey from Wall Street law firms to leadership roles in Silicon Valley’s most iconic tech companies.Shanti shares how she navigated legal practice in the early days of tech, when in-house legal teams were small or nonexistent, and how that experience shaped her strategic approach to business, compliance, and innovation. With deep experience at companies like Twilio, Zendesk, and JFrog, she opens up about translating legal risk into business value, building legal functions from scratch, and the power of understanding your product from the inside out.In this conversation, you’ll learn:What it takes to lead as the first and only in-house counsel at a public companyHow in-house legal teams have evolved in Silicon Valley over the last two decadesWhy staying close to the business and earning cross-departmental trust is keyHow to thrive in high-growth environments with complex tech stacksWhy calculated risk-taking and product fluency are essential for modern legal leadershipWhether you’re an aspiring General Counsel, early-career in-house counsel, or a legal leader navigating fast-paced industries, this episode offers practical strategies and candid insights on building legal teams, aligning with business strategy, and leading with confidence at the intersection of law and technology.

In this episode of Notes to My (Legal) Self, Olga Mack continues the Legal Operations series with Minh Merchant, a three-time General Counsel and mission-driven legal leader in the healthcare industry.In “Leading with Intent,” Minh joins Olga to unpack what it really takes to become—and remain—a public company GC. From writing earnings scripts and navigating securities disclosures to conducting career “true-up” conversations, Minh shares how she’s built a business-aligned legal path by leading with clarity, courage, and intentionality.In this conversation, you’ll learn:How to “true up” your experience when pursuing a stretch roleWhat hiring managers actually look for in a general counselThe mindset shift from qualified to capableHow to tap into your network for mentorship and accelerated growthWhy asking “Do I still want this?” is key to long-term career alignmentWhether you're preparing for a leap into a new role, transitioning into a different industry, or refining your career blueprint, Minh offers a thoughtful, practical framework for legal leadership that lasts.This episode is for:In-house counsel mapping their next moveLegal ops professionals with executive ambitionsLegal leaders seeking growth beyond traditional career laddersTune in to explore what it means to grow your legal career intentionally—on your terms, and in alignment with where you’re headed next.

The legal world can be intense—especially when you're the only lawyer in the room. In this episode, Tara Trantham joins Olga Mack to share her powerful story of navigating legal leadership, federal investigations, and mental health challenges without the safety net of a law firm or legal tech.With over 23 years as in-house counsel in financial services, Tara brings hard-won insights into how legal professionals can survive and thrive under pressure. From managing legal, compliance, and HR teams to advocating for mental health in high-stress environments, she delivers a candid look at what it takes to lead with resilience.In this conversation, you'll learn:How to survive high-stakes internal investigations as a solo GCWhy legal tech is essential—and what it costs to go without itHow to make a compelling case to the board for legal ops investmentWhat outside counsel can do to truly support in-house teamsWhy mental health advocacy is non-negotiable in today’s legal landscapeWhether you're a solo in-house lawyer, a GC managing change, or an advocate for wellness in the legal profession, this episode offers a clear, human roadmap to legal resilience and leadership.

In this episode, Tyler Quillin, Product and Regulatory Counsel at Xbox, joins Olga Mack to kick off Season 12 of Notes to My (Legal) Self with a powerful conversation on how legal professionals can better align with product teams, regulators, and executives in today’s fast-paced tech world.Drawing on his background as both an educator and in-house attorney, Tyler shares how a teaching mindset—paired with business fluency—can help legal teams collaborate more effectively, build executive trust, and deliver solutions that move the business forward.In this conversation, you'll learn:How to simplify legal guidance through analogies, visuals, and storytellingWhy early engagement with regulators can give your company a strategic edgeHow legal can say “yes” while managing risk and driving innovationPractical ways to systematize mentorship and leadership developmentHow to build trust across departments and become a true business partnerWhether you're an aspiring product counsel, a legal ops professional, or a tech-savvy in-house attorney, this episode offers a roadmap for adding real business value—without compromising on legal integrity.

Have you ever wondered how in-house legal teams can navigate the rapidly shifting landscape of AI and ESG? Join us in this episode with Christine Uri, Chief Legal and Sustainability Officer, as she reveals how legal leaders are shaping the future of their departments through innovation, governance, and purpose.In this conversation with Olga Mack, Christine shares her unconventional journey—from artificial intelligence governance to corporate sustainability—and explores how today’s legal professionals can thrive by embracing the unexpected.Tune in to discover:Why AI and ESG are no longer optional—they’re essential for legal teams.How legal leaders can balance innovation with governance.Why collaboration and proactive risk management are the keys to success.Practical steps for building effective AI oversight frameworks within legal departments.Don’t miss this chance to learn from Christine’s wealth of experience and her insights into how in-house lawyers can drive innovation while maintaining responsible oversight. Whether you're leading a legal department or just beginning your in-house journey, this episode will give you the tools to future-proof your career and your company.