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Karl explores:• Why the traditional deposition process is costly, outdated, and ready for disruption• How Skribe.ai leverages software and AI to modernize testimony capture• The nationwide shortage of stenographers, and what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 fit
Key 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 innovator
If 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, 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 take away: • 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 engineersIf 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 inequities
If 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 effectivelyIf 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
Season 13, Episode 1: The Journey to a Transparent Marketplace for Legal Services (ft. Basha Rubin)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 modelIf 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 like
How compliance careers evolve with tech innovation and global oversight
Why pro bono work builds leadership skills and business acumen
How community service can ground legal careers in purpose and perspective
What lawyers need to thrive in highly regulated, fast-paced industries
Whether 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 careers
How to transition into executive and non-legal leadership roles
The value of community engagement in long-term professional success
How to pivot your career with resilience and purpose
Why viewing yourself as a client can transform personal development
Whether 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 code
How in-house teams evaluate legal tools through a cost–value lens
Real-world use cases for GenAI—from drafting contracts to redline comparisons
How to align GenAI initiatives with company culture and strategic goals
Why GenAI should enhance human clarity, not replace legal judgment
Whether 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 strategy
How to uncover hidden business pain points—and solve them proactively
Why empowering legal team members, including paralegals, fuels innovation
What it takes to build trust and redefine the GC role as a business partner
Scalable strategies to embed legal in operations and drive business outcomes
Whether 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 it
Which key performance indicators (KPIs) lawyers should be tracking
How to structure your day for productivity and reduce burnout
The value of unstructured time—and how to protect it
How to lead through service, not just conflict
Whether 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 teams
How listening—really listening—can uncover blind spots and biases
How healthy conflict can be a catalyst for innovation and better legal outcomes
How visual and verbal cues reveal hidden assumptions about socioeconomic status
Strategies 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 company
How in-house legal teams have evolved in Silicon Valley over the last two decades
Why staying close to the business and earning cross-departmental trust is key
How to thrive in high-growth environments with complex tech stacks
Why calculated risk-taking and product fluency are essential for modern legal leadership
Whether 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 role
What hiring managers actually look for in a general counsel
The mindset shift from qualified to capable
How to tap into your network for mentorship and accelerated growth
Why asking “Do I still want this?” is key to long-term career alignment
Whether 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 move
Legal ops professionals with executive ambitions
Legal leaders seeking growth beyond traditional career ladders
Tune 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 GC
Why legal tech is essential—and what it costs to go without it
How to make a compelling case to the board for legal ops investment
What outside counsel can do to truly support in-house teams
Why mental health advocacy is non-negotiable in today’s legal landscape
Whether 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 storytelling
Why early engagement with regulators can give your company a strategic edge
How legal can say “yes” while managing risk and driving innovation
Practical ways to systematize mentorship and leadership development
How to build trust across departments and become a true business partner
Whether 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.
The future of legal education is here! In this episode, Linsey Krolik joins Olga Mack to discuss how law schools can adapt to the rapidly changing landscape of legal operations and technology. Together, they explore how GenAI, legal ops, and tech adoption should be integrated into law curricula to better prepare students for in-house roles.
Linsey shares her vision for reshaping legal education to equip the next generation of lawyers with the skills and mindset needed to thrive in modern legal departments. If you're passionate about the future of legal education, this episode is for you.
In this conversation, you'll learn:
How GenAI is reshaping legal education and what law schools can do to adapt
Why legal operations is a critical area of focus for future lawyers
How law students can develop skills that make them valuable contributors to legal tech
The importance of hands-on experience and internships in preparing for legal ops roles
Strategies for continuous learning and adapting to the changing legal tech landscape
Whether you're a legal educator, an in-house lawyer, or simply passionate about the future of legal ops, this episode will give you a roadmap for the changes needed in legal education.
Ready to make AI work for your legal team? In this episode, Navin Mahavijiyan unpacks the magic (and the challenges) of implementing and maintaining legal chatbots that are not just functional—but truly aligned with your team’s culture and tone.
Continuing our Legal Operations series, Navin joins Olga Mack to share actionable insights on designing chatbots that help, not hinder. From the first step of chatbot implementation to scaling and ongoing maintenance, Navin gives you the roadmap for making AI a trusted ally in your legal ops toolbox.
In this episode, you’ll learn:
The real first step to chatbot implementation (spoiler: it’s not technical!)
Why bot maintenance is critical for long-term success
How to humanize bots to fit your team’s unique language and values
How to use real-world scenarios to train your bot for greater impact
Why chatbots can amplify your team’s work, not replace it
If you're ready to dive into the world of legal chatbots, this episode offers everything you need—from initial setup to keeping your bot aligned with your evolving needs.
What if data could create a stronger sense of belonging in the legal profession? In this episode, Flo Nicolas shows how people analytics and bold leadership can transform legal teams from the inside out.
Continuing our Legal Operations series, Flo joins Olga Mack to share her inspiring journey from traditional law practice to becoming a trailblazer for diversity, equity, and inclusion (DEI) in legal ops. With a mix of candor and strategic wisdom, Flo breaks down how data, risk-taking, and community-building can fuel real, lasting change.
In this episode, you’ll learn:
How people analytics can power smarter, more inclusive legal operations
Why risk tolerance matters in building a modern legal career
How setbacks and failures can become stepping stones to innovation
Strategies for using data to bridge the gap between business and legal functions
Why authentic networking is key to driving legal transformation
If you're passionate about building stronger, more inclusive legal teams—or curious about how data and human capital intersect—this episode offers actionable insights and inspiration for the future of legal leadership.
Think lawyers hate legal tech? They don’t—they just don’t know how much they need it yet. In this episode, Chad Aboud reveals how to sell legal tech into corporate legal departments and drive adoption that actually sticks.
Continuing our Legal Operations series, Chad joins Olga Mack for a candid conversation about what really works (and what doesn’t) when bringing new solutions into legal teams. From building internal champions to avoiding post-sale burnout, Chad shares a playbook grounded in empathy, curiosity, and community-building.
In this episode, you’ll learn:
How to sell into legal without selling out your values
Why pre-agreeing on “wins” smooths tech rollouts
How to build first versions that leave room for growth
Ways to engage sales, finance, and account management post-sale
How to become a trusted sounding board for lonely legal teams
If you're ready to turn resistance into momentum—and move legal teams from “maybe” to “let’s go”—this episode is your essential guide. Tune in for real-world strategies, fresh perspective, and a smarter way to sell and implement legal tech.