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.

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#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.

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#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.

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#LegalInnovation #ProductManagement #LegalEmail #FutureOfLaw #NotesToMyLegalSelf