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 into a strategic lever for speed, talent, and innovation, legal teams are being asked to rethink how these deals are structured and managed in practice.

Irina shares how AI is reshaping outsourcing relationships, why governance and incentives matter more than lengthy contracts, and how in-house counsel can design vendor ecosystems that are resilient, adaptive, and aligned with business reality.

Takeaways:• Outsourcing is no longer about cost, it’s about capability and speed• AI is fundamentally reshaping vendor relationships and service models• Governance and incentives often matter more than contract language• Operational reality must inform legal structure• In-house counsel must evolve into strategic business partners

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 depositions play a decisive role.

Dean introduces the concept of the “Fourth Closing Argument” and explains how real-time transcription, AI, and legal tech are transforming deposition strategy, risk management, and expectations of legal competence.

Takeaways:

• Depositions are no longer procedural, they are decisive

• Discovery is where cases are won or lost

• Real-time insight improves precision and litigation strategy

• Legal tech is reshaping expectations of competence

• Strategic depositions create measurable advantage

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 she built from a passion project into a thriving business later acquired by DocuSign.Jessica Nguyen is Deputy General Counsel at DocuSign and Head of Contract Nerds, with a track record of building legal teams and scaling legal technology companies from early-stage startups to successful exits.

Key insights from this episode:

• How side hustles can evolve into strategic business assets

• Why email lists and community ownership matter more than social followers

• How to evaluate risk as an in-house lawyer• What founders should consider before selling their business

• The emotional realities of acquisitions, and how to navigate them

• Why lawyers must rethink risk aversion and embrace upside

This episode is for in-house lawyers, founders, legal operators, and anyone wondering whether they can build something meaningful beyond their role without walking away from it.

Takeaways:

• Build with generosity first, monetization follows value

• Strategic partnerships matter more than short-term offers

• Preparation and organization accelerate opportunity

• Lawyers are uniquely equipped to build, if they embrace the upside.

• Alignment beats adrenaline in both business and life.

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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 preserve, replicate, and even converse with digital versions of ourselves.

Together, they explore:

• Why AI forces us to confront legacy in ways social media never did• The concept of “conversational time travel” and digital personas of the past and future

• How companies may face a two-market reality: privacy as default vs. privacy as luxury

• The hidden risks of unintentional AI adoption inside organizations

• Why in-house counsel must move from reactive policy drafting to intentional AI governance

If you’re an in-house lawyer navigating AI implementation or questioning how emerging technologies will reshape privacy, identity, and ethics, this conversation challenges you to think several steps ahead.

Explore more episodes, insights, and reflections at:

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#NotesToMyLegalSelf #AI #LegalInnovation #InHouseCounsel #AIGovernance #DigitalLegacy

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 growth

If 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 adoption

If 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 revolution

Key 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 it

If 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 issues

Key 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 build

If 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